m-Chloroperbenzoic acid → HCID 11121760、化合物

HRID 1490347ノート

反応式

HRID 1490347 の反応式
ClC1C=C(C=CC=1)C(OO)=[O:6].[Si:12]([O:19][C@@H:20]([C@@H:22]1[C@@H:25]([S:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:24][C:23]1=[O:33])[CH3:21])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)Cl>[Si:12]([O:19][C@@H:20]([C@@H:22]1[C@@H:25]([S:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:6])[NH:24][C:23]1=[O:33])[CH3:21])([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 11089029HCID 11089029、化合物

生成物 1

HCID 11121760HCID 11121760、化合物収率 90.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

1.5 g of 3-chloroperoxybenzoic acid was added, whilst ice-cooling, to a solution of 2 g of (3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-phenylthio-2-azetidinone [prepared as described in step (i) above] in 30 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 6 hours. At the end of this time, the reaction mixture was mixed with 30 ml of methylene chloride, and the organic layer was separated and washed with water, with a saturated aqueous solution of sodium hydrogencarbonate and again with water, in that order. It was then dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash chromatography, using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the eluent, to give 1.9 g of the title compound consisting of two diastereomers, differing in the configuration of the sulfoxide group, as colorless crystals, melting at 65°-70° C.

後処理

  1. customthe organic layer was separated
  2. washwashed with water, with a saturated aqueous solution of sodium hydrogencarbonate and again with water, in that order
  3. dry with materialIt was then dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by flash chromatography
  6. additionby volume mixture of cyclohexane and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-a352c756318f47e9ae6ad902f0e48437
出典データセット
uspto-grants-1997_10
特許番号
US05681951

反応ノート

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