2-Benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane → (4-Benzenesulfonyl-1-benzyl-2-hydroxy-7-methyl-octyl)carbamic acid benzyl ester

HRID 2120412ノート

反応式

HRID 2120412 の反応式
[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].C([Li])CCC.[CH2:21]([O:28][C:29](=[O:42])[NH:30][CH:31]([CH:39]1[CH2:41][O:40]1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:21]([O:28][C:29](=[O:42])[NH:30][CH:31]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:39]([OH:40])[CH2:41][CH:5]([S:6]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:7])=[O:8])[CH2:4][CH2:3][CH:2]([CH3:15])[CH3:1])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

5

反応物 3

HCID 148872432-Benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butaneHCID 23439301(4-Methyl-pentane-1-sulfonyl)-benzeneHCID 178418339Butyllithium

生成物 1

HCID 69689188(4-Benzenesulfonyl-1-benzyl-2-hydroxy-7-methyl-octyl)carbamic acid benzyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3.0 equivalents of (4-methyl-pentane-1-sulfonyl)-benzene (previously prepared by Gaoni, J. Org. Chem. 1982, 47, 2564) in tetrahydrofuran cooled to −78° C. is added 3.0 equivalents of n-butyl lithium and stirred for 30 min. One equivalent of (1-oxiranyl-2-phenyl-ethyl)-carbamic acid benzyl ester (previously prepared by Kaldor, et al. J. Med. Chem., 1997, p. 3979) in THF is then added dropwise and the reaction stirred for 1.5 h. The reaction is then quenched with saturated aqueous sodium bicarbonate and warmed to ambient temperature. After standard aqueous work-up and extraction, followed by concentration and silica gel chromatography the title compound is obtained.

後処理

  1. stirringthe reaction stirred for 1.5 h
  2. customThe reaction is then quenched with saturated aqueous sodium bicarbonate
  3. extractionAfter standard aqueous work-up and extraction
  4. concentrationfollowed by concentration and silica gel chromatography the title compound
  5. customis obtained

出典と根拠

ORDレコード
ord-1e21502215ec4100babe3605def175a1
出典データセット
uspto-grants-2004_02
特許番号
US06689886B2

反応ノート

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