[(S)-2-(3,5-Bis-trifluoromethyl-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl ester → (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one

HRID 456218노트

반응식

HRID 456218 반응식
C([O:8][C:9](=O)[NH:10][C@@H:11]([CH3:28])[CH:12]([C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)[OH:13])C1C=CC=CC=1.[OH-].[K+].C1COCC1.CO>CCOC(C)=O.[Cl-].[Na+].O>[F:26][C:24]([F:25])([F:27])[C:16]1[CH:15]=[C:14]([C@H:12]2[O:13][C:9](=[O:8])[NH:10][C@H:11]2[CH3:28])[CH:19]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:17]=1

참가 물질

5

반응물 2

HCID 58604019[(S)-2-(3,5-Bis-trifluoromethyl-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl esterHCID 86630533KOH MeOH THF

생성물 1

HCID 23583229(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

To [(S)-2-(3,5-bis-trifluoromethyl-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl ester (11.9 mmol) was added 7.5N aqueous KOH:THF:MeOH (1:4:2; 60 mL), and the reaction was stirred at room temperature for 3 hours. Once no starting material was seen by analytical LCMS, the mixture was diluted with EtOAc and brine, and the organic layer was separated and purified by silica gel chromatography to give the title compound.

후처리

  1. customthe organic layer was separated
  2. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-beff7375a8644ed6a23dc488e130ca14
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497381B2

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