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

HRID 1266665Notes

Reaction equation

HRID 1266665 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ce22cee819d41ee992273d6012b7935
Source dataset
uspto-grants-2003_04
Patent number
US06548671B2

Reaction notes

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