Trichloroisocyanuric Acid → (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732381노트

반응식

HRID 732381 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]1[C@H:14]1[O:18][C:17]([CH3:20])([CH3:19])[N:16]([C:21](=[O:23])[CH3:22])[C@H:15]1[CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.CC1(C)N([O])C(C)(C)CCC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[O:13])[CH2:10][C@@H:9]1[C@H:14]1[O:18][C:17]([CH3:19])([CH3:20])[N:16]([C:21](=[O:23])[CH3:22])[C@H:15]1[CH2:24][C:25]1[CH:26]=[C:27]([F:32])[CH:28]=[C:29]([F:31])[CH:30]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 68814386(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 68814480(R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester수율 100.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Cool to 0° C. a solution of (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.01 gr, 0.022 mmol) in dichloromethane (0.5 mL). Add trichloroisocyanuric acid (0.023 g, 0.110 mmol). Stir 5 minutes and then add TEMPO (2,2,6,6-tetramethyl-1-piperidinyl-oxy, free radical, 0.0007 g, 0.0044 mmol). After one hour add dichloromethane to the mixture and wash with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride. Dry over magnesium sulfate and concentrate under reduced pressure to provide the desired compound (0.010 g, 95%).

후처리

  1. washwash with saturated aqueous sodium bicarbonate
  2. dry with materialDry over magnesium sulfate
  3. concentrationconcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-767cbb593110495cb8896e6e4f5553a6
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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