Heterocyclic Building Blocks-Oxazolidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108149-63-9,(R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate,as a common compound, the synthetic route is as follows.

Dibenzyl diisopropylphosphoramidite (1.067 mL, 3.24 mmol) is added to compound 8540,41 (0.5 g, 2.162 mmol) and 1H-tetrazole (0.454 g, 6.49 mmol) in CH3CN (10 mL) and the mixture stirred for 1 h. The solvent is evaporated and the residue flash chromatographed (EtOAc-hexanes, 1:9 v/v) to give tert-butyl (4R)-4-({[bis(benzyloxy)phosphanyl]oxy}methyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate as a colourless oil. This is dissolved in CH2Cl2 (10 mL) cooled in ice-water and MCPBA (m-chloroperoxybenzoic acid) (0.995 g, 4.32 mmol) added and stirred for 30 min. The mixture is diluted with CH2Cl2 (50 mL) and washed with satd aq Na2SO3, satd aq NaHCO3 (3*) then brine, dried and the solvent evaporated. The residue is flash chromatographed (DCM-hexanes-EtOAc, 4:3:1 v/v/v) to give tert-butyl (4R)-4-({[bis(benzyloxy)phosphoryl]oxy}methyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate as a colourless oil (0.816 g, 77%). [alpha]22D +21.5 (c 0.57, CHCl3). 1H NMR (500 MHz, CDCl3) 7.34 (s, 10H), 5.08-5.00 (m, 4H), 4.22-4.16 (m, 0.5H), 4.13-4.06 (m, 1H), 3.97-3.83 (m, 3H), 3.77 (q, J = 8.6, 0.5H), 1.52-1.41 (m, 15H). 13C NMR (125.7 MHz) 152.1, 151.4 (C), 135.7 (C), 128.6 (CH), 127.9 (CH), 94.1, 93.6 (C), 80.6, 80.3 (C), 69.4 (CH2), 65.7, 65.3 (CH2), 64.8, 64.6 (CH2), 56.6, 56.5, 56.32, 56.26 (CH), 28.3 (CH3), 27.4, 24.3 (CH3), 26.6, 23.0 (CH3). Referenced to the centre line of CDCl3 at delta 77.0. 31P NMR (202.3 MHz, CDCl3) -1.0 (s), -1.1 (s). ESI-HRMS for C25H34NNaO7P [M+Na]+ calcd 514.1971; found 514.1968. This material (0.77 g, 1.567 mmol) and 10% Pd-C (100 mg) are stirred in EtOH (15 mL) under a hydrogen atmosphere at ambient temperature and pressure for 16 h. The mixture is filtered through cellulose paper and the solvent is evaporated to give {[(4R)-3-[(tert-butoxy)carbonyl]-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}phosphonic acid as a colourless gum (480 mg). This is dissolved in 80% aq TFA (10 mL) and left at room temperature for 2 h. The solvent is evaporated and the residue dissolved in H2O (10 mL) and washed with CH2Cl2 (2 * 10 mL) then evaporated. The residue is dissolved in H2O and chromatographed on RP 18 silica gel (H2O) to give 86 as a colourless gum which solidified (0.26 g, 97%). [alpha]22D 0 (c 0.565, H2O). No measurable rotation observed. 1H NMR (500 MHz, D2O) 4.19-4.12 (m, 1H), 4.11-4.03 (m, 1H), 3.90 (dd, J = 12.3, 4.7, 1H), 3.81 (dd, J = 12.3, 6.7, 1H), 3.63 (m, 1H). Referenced to HOD at delta 4.79. 13C NMR (125.7 MHz, D2O) 62.9 (d, J = 3.2, CH2), 59.1 (CH2), 53.5 (d, J = 7.4, CH). Referenced to internal CH3CN at delta delta 1.47. 31P NMR (202.3 MHz, D2O) 0.0 (s). ESI-HRMS for C3H9NO5P [M-H]- calcd 170.0218; found 170.0211.

108149-63-9, As the paragraph descriping shows that 108149-63-9 is playing an increasingly important role.

Reference£º
Article; Clinch, Keith; Crump, Douglas R.; Evans, Gary B.; Hazleton, Keith Z.; Mason, Jennifer M.; Schramm, Vern L.; Tyler, Peter C.; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5629 – 5646;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

497-25-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.497-25-6,Oxazolidin-2-one,as a common compound, the synthetic route is as follows.

Example 101 (R) and (S) -3- (5′-fluoro-2,2-dimethyl-2′-oxospiro [cyclopropane- 1 ,3′-hidoline] – 1 ‘-yl) -5- (2-oxooxazolidin-3-yl)benzoic acidSynthesis of methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoateA suspension of 3-bromo-5-iodo-benzoic acid methyl ester (682 mg, 2 mmol), oxazolidin- 2-one (191 mg, 2.2 mmol), Cul (76 mg, 0.4 mmol), potassium carbonate (545mg, 4mmol) and N, N’-dimethyl-ethane-l,2-diamine (86uL, 0.8mmol) in acetonitrile (15 mL) was stirred for 16 hours at 90C. The precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford 3-bromo-5-(2-oxo-oxazolidin-3-yl)- benzoic acid methyl ester (480 mg, 80%) which was used for next step without further purification.

The synthetic route of 497-25-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; FENG, Lichun; HE, Yun; HUANG, Mengwei; YUN, Hongying; WO2011/70039; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,95715-86-9

Step 3: Preparation of (S)-3 -(tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4- carboxylic acid (Intermediate 4) To a solution of (5)-3-tert-butyl-4-methyl 2,2-dimethyloxazolidine-3,4- dicarboxylate (6.75 g, 26.0 mmol) in THF (80 mL) and water (40 mL) was added lithium hydroxide hydrate (1.20 g, 28.6 mmol) at room temperature. The reaction mixture was. stirred for 12 hours at room temperature. After evaporation of volatile solvents, the residue was diluted with EtOAc, neutralized with 2 N aq. HC1, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to obtain the title compound (6.32 g, 99%), which was used for the next reaction without further purification.?H-NMR (400 MHz, CDC13): (two sets of rotamers) 4.40-4.5 1 (m, 1H),4.17-4.28 (m, 1H), 4.11-4.15 (m, 1H), 1.62 and 1.67 (s and s, 3H), 1.51 and 1.54 (s and s, 3H), 1.43 and 1.51 (s and s, 9H).

95715-86-9 Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate 688220, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; KAINOS MEDICINE, INC.; OH, Su-Sung; CHOI, Minjeong; WO2015/156601; (2015); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

90719-32-7, (S)-4-Benzyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

90719-32-7, [00177] Results: Synthesis of the propionyl oxazolidinone 4 was accomplished without the requirement of a highly reactive base (Ho, G-J et al. J. Org. Chem. 60, 2271-2273 (1995)) and subsequent stereoselective aldol reaction with methacrolein (Nielsen, P. E. Chem. Biodivers. 7, 786-804 (2010)) was achieved under reaction conditions that do not require pre-generation of a metal enolate (Evans, D. A et al. J. Am. Chem. Soc. 124, 392-393 (2002)). Isolated by simple extraction, the TMS-ether 7 was converted to the stereodefmed allylic chloride 8 by Nb-mediated stereoselective halogenation (E:Z > 20: 1) (Ravikumar, P. C. et al. J. Org. Chem. 74, 7294-7299 (2009)). While seemingly difficult to accomplish in a highly selective fashion, hydrolysis of the imide proceeded uneventfully (without significant hydrolysis of the allylic chloride) and delivered 1 in >95% ee and 41% overall yield. Notably, this synthesis procedure delivers optically active 1 in acceptable yield and purity through a four-step sequence that does not require a single chromatographic operation. As an indication of the robust nature of this sequence, lOg of 4 was converted to ca. 4g of 1 routinely.

90719-32-7 (S)-4-Benzyloxazolidin-2-one 736225, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; THE SCRIPPS RESEARCH INSTITUTE; MICALIZIO, Glenn, C.; KODADEK, Thomas; SARKAR, Mohosin; WO2013/36753; (2013); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.139009-66-8,(S)-N-Boc-2,2-dimethyloxazolidine-4-carboxylic Acid,as a common compound, the synthetic route is as follows.

General procedure: Following the general procedure, the reactionwas carried out starting from carboxylic acid 5 (735 mg, 3 mmol), EDC (630 mg, 3.1 mmol), HOBT (504 mg, 1.1mmol), 1-pentadecyne (1.872 g, 9 mmol) and n-butyllithium(576 mg, 9 mmol), to give 783 mg of ynone 7as an oil (60% yield). TLC (Hexane-AcOEt 85:15) RF 0.50. [a]D-51.9(c 2.0 in CHCl3). 1H NMR(300 MHz, CDCl3): d 4.34(dd, 1H, J = 7.4,3.8 Hz) 4.14 (dd, 1H, J =9.4, 7.4 Hz), 4.05 (dd, 1H, J =9.4, 3.8 Hz), 2.37 (t, 2H, J = 6.9), 1.69 (s, 3H), 1.53 (s, 3H), 1.49 (m, 4H), 1.45 (s, 9H),1.24 (m, 18H), 0.87 (t, 3H, J = 7.2Hz). 13CNMR (75 MHz, CDCl3): delta 186.2, 127.9, 98.1, 95.3,80.6, 66.5, 65.7, 65.3, 51.6, 31.8, 29.5, 29.4, 29.3, 28.9, 28.8, 28.3, 28.1,27.5, 26.1, 25.1, 25, 24.2, 22.6, 19, 14. Anal.Calcd. For C26H45NO4: C, 71.68; H, 10.41; N,3.22. Found: C, 71.66; H, 10.40; N, 3.21

139009-66-8, As the paragraph descriping shows that 139009-66-8 is playing an increasingly important role.

Reference£º
Article; Morales-Serna, Jose Antonio; Sauza, Alejandro; Padron De Jesus, Gabriela; Gavino, Ruben; Garcia De La Mora, Gustavo; Cardenas, Jorge; Tetrahedron Letters; vol. 54; 52; (2013); p. 7111 – 7114;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.497-25-6,Oxazolidin-2-one,as a common compound, the synthetic route is as follows.

497-25-6, 4-Fluoro-2-(2-oxooxazolidin-3-yl)bejizonitrile. A 48 mL pressure vessel containing 2-bromo-4-fluorobenzonitrile (1.00 g, 5.00 mmol), 2-oxazolidone (0.390 g, 4.50 mmol), K2CO3 (0.970 g, 7.0 mmol) and xantphos (0.231 g, 0.40 mmol) in dioxane (10 mL) was degassed with argon for 15 min. Pd2dba3 (0.140 g, 0.15 mmol) was introduced and then the reaction mixture was heated at 70 0C for 18 h. The mixture was cooled, diluted with dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and subjected to column chromatography on silica gel with hexanes-.ethyl acetate (1:1) to (3:7) gradient as the eluent to afford the title compound as a white solid (0.460 g, 50% yield): 1H NMR (400 MHz, CDCl3) delta ppm: 7.73 (IH, dd, J = 5.8, 8.6 Hz), 7.43 (IH, dd, J = 2.5, 9.6 Hz), 7.11 (IH, ddd, J = 2.5, 7.5, 8.7 Hz), 4.60 (2H, t, J = 7.1 Hz), 4.29 (2H, t, J = 7.1 HJz); LCMS f ESI, M+H*) m/z 207.

As the paragraph descriping shows that 497-25-6 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

16251-45-9, (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 38 [4S-(4alpha,5alpha)]3-(3-Furan-2-yl-propionyl)-4-methyl-5-phenyl-oxazoldin-2-one Compound 29 (11.66 g, 83.19 mmol) was dissolved in THF (190 ML) and cooled in an ice bath.. triethyl amine (43.5 ML, 312.1 mmol) was added, followed by the trimethylacetyl chloride (15.4 ML, 125.0 mmol).. The reaction was stirred at 0 C. for 2 hours, and the LiCl (3.879 g, 91.5 mmol), (4S,5R)-(-)-4-methyl-5-phenyl-2-oxazolidinone (15.02 g, 84.76 mmol), and THF (70 ML) were added.. The reaction was stirred at room temperature overnight.. The solids were filtered, washed with EtOAc, and the filtrate and washings rotovapped to give a brown colored suspension.. The solids were filtered, washed with EtOAc, and the filtrated rotovapped.. The crude material was chromatographed on silica eluding with 10% EtOAc/hexanes to give the title compound 38 (19.967 g, 80%) as an off-white solid. 1H NMR (400 MHz, CDCl3) delta7.42-7.33 (m, 3H), 7.29-7.24 (m, 3H), 6.26 (m, 1H), 6.04 (d, 1H, J=3.17), 5.65 (d, 1H, J=7.33 Hz), 4.74 (q, 1H, J=6.8 Hz), 3.35-3.21 (m, 2H, 3.01 (t, 2H, J=7.4 Hz), 0.87 (d, 3H, J=6.59 Hz). MS (APCI) m/z 300 (M++1). Analysis calculated for C17H17NO4: C, 68.22; H, 5.72; N, 4.68. Found: C, 68.34; H, 5.81; N, 4.63. [alpha]D=-39.5 (c=1 in CHCl3).

16251-45-9, As the paragraph descriping shows that 16251-45-9 is playing an increasingly important role.

Reference£º
Patent; Warner-Lambert Company; US6710190; (2004); B1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

Example 11 A mixture of (E)-4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]cinnamaldehyde (2.00 g), 2,4-oxazolidinedione (1.11 g), piperidine (0.23 g), ethanol (100 ml) and tetrahydrofuran (50 ml) was refluxed under heating conditions for 8 hours. After the reaction mixture was concentrated, chloroform was added to the residue; the mixture was then washed with 2N HCl and water. The organic layer was washed with water, dried (MgSO4) and then concentrated. The residue was subjected to silica gel column chromatography. The crystal obtained from the fraction eluted with ethyl acetate-chloroform (1:9, v/v) was dissolved in tetrahydrofuran (100 ml), and subjected to catalytic hydrogenation at 1 atm and room temperature in the presence of palladium-carbon (5%, 0.5 g). After the catalyst was filtered off, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to yield 5-[3-[4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]ethyl]phenyl]propyl]-2,4-oxazolidinedione (0.29 g, 12%) from the fraction eluted with methanol-chloroform (2:98, v/v), which was then recrystallized from dichloromethane-isopropyl ether to yield a colorless prisms having a melting point of 168-169 C.

2346-26-1, The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5614544; (1997); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

WORKING EXAMPLE 23 In substantially the same manner as in Working Example 11, 4-methoxy-3-(5-methyl-2-phenyl-4-oxazolyl-methoxy)cinnamaldehyde was condensed with 2,4-oxazolidinedione. The condensate was subjected to catalytic reduction to yield 5-[3-[4-methoxy-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propyl]-2,4-oxazolidinedione, which was recrystallized from chloroform-methanol to give colorless prisms, m.p.185-187 C.

2346-26-1, 2346-26-1 Oxazolidine-2,4-dione 97389, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5932601; (1999); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

452339-73-0, (R)-5-(2,2-Dimethyl-4H-benzo[d][1,3]dioxin-6-yl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Sodium hydride (60% oil dispersion, 1.4g) was added to a stirred solution of (5R)- (2, 2- DIMETHYL-4H-1, 3-BENZODIOXIN-6YL)-1, 3OXAZOLIDIN-2-ONE (6. 0G) in dry dimethylformamide (80ML) at 0 under nitrogen. After 20 min a solution of 1- {4- [ (6-BROMOHEXYL) oxy] butyl}-4- iodobenzene (12.6g) in dry dimethylformamide (30ML) was added dropwise. The mixture was stirred for 15h at ambient temperature. The mixture was poured into an aqueous ammonium chloride solution (700MI) and extracted into ethyl acetate. The organic extracts were washed with water, dried (NA2SO4) and evaporated. Purification by chromatography on a biotage cartridge (90g) using ether-petroleum ether (40-60) (4: 1) gave the title compound as a clear oil (10G). LCMS RT = 4.19 min.

452339-73-0, As the paragraph descriping shows that 452339-73-0 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/39762; (2004); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem