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

HRID 622442ノート

反応式

HRID 622442 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b303b213974a42bab756c8ca0a7866df
出典データセット
uspto-grants-1988_09
特許番号
US04771046

反応ノート

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