(4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester

Base Information

• Chemical Name: (4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester
• CAS No.: 218902-08-0
• Molecular Formula: C₁₅H₁₄ClFN₂O₈
• Molecular Weight: 404.736

Synonyms:(4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester

Chemical Property of (4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester

Chemical Property:

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Technology Process of (4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester

There total 5 articles about (4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(4S,5R)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-(3-chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester (218902-04-6) → (4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester (218902-08-0)

Guidance literature:

With lithium hydroperoxide; at -5 ℃; Yield given;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester (218902-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP / CH₂Cl₂

2: HCO₂H, H₂O₂ / H₂O

3: LiOOH / -5 °C

With dmap; formic acid; lithium hydroperoxide; dihydrogen peroxide; In dichloromethane; water;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

Reference yield:

3-chloro-4-fluoro-5-nitro-benzaldehyde → (4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester (218902-08-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) THF, -78 deg C

2: DMAP / CH₂Cl₂

3: HCO₂H, H₂O₂ / H₂O

4: LiOOH / -5 °C

With 1-ethyl-piperidine; dmap; tin(II) trifluoromethanesulfonate; formic acid; lithium hydroperoxide; dihydrogen peroxide; In dichloromethane; water;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

upstream raw materials:

(4S,5R)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-(3-chloro-4-fluoro-5-nitro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

(S)-4-Benzyl-3-[(4S,5R)-5-(3-chloro-4-fluoro-5-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one

Downstream raw materials:

(4S,5R)-5-(3-Chloro-4-fluoro-5-nitro-phenyl)-4-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

((1S,2R)-2-(3-Chloro-4-fluoro-5-nitro-phenyl)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-hydroxy-ethyl)-carbamic acid tert-butyl ester

[(R)-(2-Benzyloxy-4-methoxy-phenyl)-((1S,2R)-2-(3-chloro-4-fluoro-5-nitro-phenyl)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-hydroxy-ethylcarbamoyl)-methyl]-carbamic acid tert-butyl ester

(2S,3R)-2-[(R)-2-(2-Benzyloxy-4-methoxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(3-chloro-4-fluoro-5-nitro-phenyl)-N-[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-3-hydroxy-propionamide

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