1H-1,2,4-Triazole → [(1R,2S)-1-Benzyl-2-hydroxy-3-[1,2,4]triazol-1-yl-propyl]-carbamic acid tert-butyl ester

HRID 424985

Reaction equation

HRID 424985 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([C@@H:16]1[CH2:18][O:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1>>[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@@H:16]([OH:17])[CH2:18][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 11357515erythro-N-Boc-D-phenylalanine epoxide

Product 1

HCID 66703587[(1R,2S)-1-Benzyl-2-hydroxy-3-[1,2,4]triazol-1-yl-propyl]-carbamic acid tert-butyl ester

Procedure

Using general procedure 4 with [(1R)-1-{(2R)-oxiran-2-yl}-2-phenyl-ethyl]carbamic acid tert-butylester (0.125 g, 0.47 mmol) and 1,2,4-triazole (0.036 g, 0.52 mmol) gives the title compound (recrystallized from ethyl acetate).

Sources & evidence

ORD record
ord-0dcba0a512df481fa14f190895fc4b44
Source dataset
uspto-grants-2012_01
Patent number
US08106090B2

Linked notes

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