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

HRID 2120412노트

반응식

HRID 2120412 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e21502215ec4100babe3605def175a1
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06689886B2

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