m-Chloroperbenzoic acid → p-Nitrobenzyl(1RS,5S,6S)-2-phenylsulfinyl-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 622442노트

반응식

HRID 622442 반응식
C(=O)(O)[O-:2].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[C:17]1([S:23][C:24]2[CH:25]([CH3:48])[C@@H:26]3[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:27]3[C:28]=2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:17]1([S:23]([C:24]2[CH:25]([CH3:48])[C@@H:26]3[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:27]3[C:28]=2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])=[O:2])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22839821p-Nitrobenzyl (1RS,5S,6S)-2-phenylthio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

생성물 1

HCID 22839820p-Nitrobenzyl(1RS,5S,6S)-2-phenylsulfinyl-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

19 ml of saturated aqueous sodium bicarbonate solution and a solution of 350 mg of 3-chloroperbenzoic acid in 10 ml of methylene chloride were added to a solution of 360 mg of p-nitrobenzyl(1RS,5S,6S)-2-phenylthio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate in 19 ml of methylene chloride, kept at 0° to 5° C. with ice-water cooling, and the mixture was stirred for 35 minutes at the same temperature. The reaction mixture was then diluted with methylene chloride and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by chromatography on a column of silica gel, using a 1/8 mixture of benzene and ethyl acetate as eluent, giving 200 mg of the title compound.

후처리

  1. washwashed with saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by chromatography on a column of silica gel
  5. additiona 1/8 mixture of benzene and ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-b303b213974a42bab756c8ca0a7866df
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04771046

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