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

HRID 2120412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2120412
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1e21502215ec4100babe3605def175a1
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06689886B2

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