Simple exploration of (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one

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Synthesis of optically active 2-piperidylglycine

Both chiral threo- and erythro-2-piperidylglycines were synthesized from racemic 2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid. (4S,5S)-4- Methyl-5-phenyl-2-oxa-zolidinone was used as a chiral auxiliary in the resolution and azidation.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2151NO – PubChem

 

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16251-45-9, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.16251-45-9, Name is (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one, molecular formula is C10H11NO2. In a article£¬once mentioned of 16251-45-9

Convenient and practical alkynylation of heteronucleophiles with copper acetylides

Copper acetylides, readily available reagents which are characterized by their lack of reactivity, can be simply activated by oxidation with oxygen in the presence of simple nitrogen ligands such as TMEDA or imidazole derivatives. Upon activation, these nucleophilic species undergo a formal umpolung and can transfer their alkyne subunit to a wide range of heteronucleophiles, including amides, oxazolidinones, imines, and dialkyl phosphites. This alkynylation, which provides one of the most practical entry to useful building blocks such as ynamides, ynimines, and alkynylphosphonates, proceeds under especially mild conditions and can be easily performed on a multigram scale. Georg Thieme Verlag Stuttgart, New York.

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Oxazolidine – Wikipedia,
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Chemoselective N-acylation of indoles and oxazolidinones with carbonylazoles

Unique reactivity: In the presence of more reactive amine and alcohol functional groups and of carboxylic acids, the chemoselective N-acylation of indoles (see scheme) and oxazolidinones is achieved by taking advantage of the unique reactivity of carbonylazole acylating agents with catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Copyright

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FATTY ACID DERIVATIVES FOR TREATING NON-ALCOHOLIC STEATOHEPATITIS

The present disclosure provides a compound for use in therapeutic and/or prophylactic treatment of non-alcoholic steatohepatitis (NASH) and/or alcoholic steatohepatitis (ASH). The compound for use according to the invention, is an unsaturated fatty acid with an oxygen incorporated in the beta-position, and further comprising an alpha-substituent. More particularly, the invention provides a compound for use in treatment of NASH and/or ASH, and a method using this, wherein the compound is of Formula (II), wherein R1, R2, R3, X, and Y are as defined in the specification; and wherein this compound may be administered alone or in combination with an additional active agent.

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.16251-45-9, Name is (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one, molecular formula is C10H11NO2, 16251-45-9. In a Article, authors is Suenaga, Kiyotake£¬once mentioned of 16251-45-9

Aurilide, a cytotoxic depsipeptide from the sea hare Dolabella auricularia: Isolation, structure determination, synthesis, and biological activity

The bioassay-guided fractionation of the cytotoxic constituents of the Japanese sea hare Dollabella auricularia led to the isolation of aurilide (1), a 26-membered cyclodepsipeptide. The gross structure of 1 was established by spectroscopic analysis including 2D NMR techniques. The absolute stereostructure was determined by chiral HPLC analysis of acid hydrolysates of 1 and by the enantioselective synthesis of a degradation product arising from a dihydroxylated fatty acid portion. The enantioselective synthesis of 1 was achieved in 12% overall yield (16 steps) and confirmed the absolute stereostructure of 1. The cytotoxicity of 1 was evaluated using a synthetic sample, which was found to exhibit potent cytotoxicity against HeLa S 3 cells with an IC50 of 0.011 mug/mL. Further biological and pharmacological studies of 1 have been carried out by using synthetic 1. Graphical abstract.

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2a (4S,5R)-3-(Bromoacetyl)-4-methyl-5-phenyloxazolidin-2-one Production is carried out analogously to Example 1a) starting from (4S,5R)-4-methyl-5-phenyloxazolidin-2-one. The coverage of NMR is identical to 1a)., 16251-45-9

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Reference£º
Patent; KLAR, ULRICH; SCHWEDE, WOLFGANG; SKUBALLA, WERNER; BUCHMANN, BERND; US2003/144523; (2003); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

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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).

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

 

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The synthetic route of 16251-45-9 has been constantly updated, and we look forward to future research findings.

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

2a (4S,5R)-3-(Bromoacetyl)-4-methyl-5-phenyloxazolidin-2-one Production is carried out analogously to Example 1a) starting from (4S,5R)-4-methyl-5-phenyloxazolidin-2-one. The coverage of NMR is identical to 1a)., 16251-45-9

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Reference£º
Patent; KLAR, ULRICH; SCHWEDE, WOLFGANG; SKUBALLA, WERNER; BUCHMANN, BERND; US2003/144523; (2003); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16251-45-9,(4S,5R)-4-Methyl-5-phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Example 32e (4S,5R)-3-(Bromoacetyl)-4-methyl-5-phenyloxazolidin-2-one 82 ml of a 2.5 molar solution of butyllithium in hexane is added to a solution of 33.06 g (186.6 mmol) of (4S,5R)-4-methyl-5-phenyloxazolidin-2-one in 500 ml of tetrahydrofuran within 30 minutes at -70 C. under argon. Then, a solution of 15.55 ml (187 mmol) of bromoacetyl chloride in 250 ml of tetrahydrofuran is added in drops in such a way that the internal temperature does not exceed -65 C. Then, it is stirred for one more hour at -70 C. Then, the reaction mixture is poured onto 50 ml of saturated aqueous ammonium chloride solution. 90 ml of saturated aqueous sodium bicarbonate solution is then added, allowed to come to 25 C., diluted with water and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, dried on sodium sulfate and chromatographed on silica gel. 42.32 g (76%) of the title compound is obtained. 1H-NMR (CDCl3): delta=0.95 (3H), 4.57 (2H), 4.80 (1H), 5.76 (1H), 7.2-7.5 (5H) ppm.

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Reference£º
Patent; KLAR, ULRICH; SCHWEDE, WOLFGANG; SKUBALLA, WERNER; BUCHMANN, BERND; US2003/144523; (2003); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem