Methanol → 4-Nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

HRID 1490362노트

반응식

HRID 1490362 반응식
O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[CH2:15]([N:17]([CH2:56][CH3:57])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][C:27]1[C@H:28]([CH3:55])[C@@H:29]2[C@@H:46]([C@H:47]([O:49][Si](C)(C)C)[CH3:48])[C:45](=[O:54])[N:30]2[C:31]=1[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33])=[O:19])[CH3:16].CO>C(Cl)Cl>[CH2:56]([N:17]([CH2:15][CH3:16])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][C:27]1[C@H:28]([CH3:55])[C@@H:29]2[C@@H:46]([C@H:47]([OH:49])[CH3:48])[C:45](=[O:54])[N:30]2[C:31]=1[C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)=[O:33])=[O:19])[CH3:57]

참가 물질

5

반응물 3

HCID 887MethanolHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 99607884-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate

생성물 1

HCID 570929914-Nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylate수율 102.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

41 mg (0.195 mmol) of citric acid hydrate were added to 30 ml of a solution of 1.072 g (1.71 mmol) of 4-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 34) in a 2:1 by volume mixture of methanol and methylene chloride, and the mixture was stirred for 20 minutes at room temperature. At the end of this time, the reaction solution was condensed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 25 g of silica gel. Elution with ethyl acetate afforded 970 mg (quantitative yield) of the title compound as a colorless foam-like solid.

후처리

  1. customcondensed
  2. distillationby distillation under reduced pressure
  3. customThe resulting residue was purified by column chromatography through 25 g of silica gel
  4. washElution with ethyl acetate

출처 및 근거

ORD 기록
ord-0a0b2724d3624fdd83e2633174bc0cba
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05681951

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