Ethyl bromodifluoroacetate → 4-Benzyloxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxypentanoic acid, ethyl ester

HRID 1196464Notes

Reaction equation

HRID 1196464 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH:20]=[O:21])[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:23]([F:30])([F:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>[Zn]>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[CH:20]([OH:21])[C:23]([F:30])([F:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69585Ethyl bromodifluoroacetateHCID 10869979N-benzyloxycarbonyl-3-cyclohexylalaninal

Product 1

HCID 141420824-Benzyloxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxypentanoic acid, ethyl esterYield 37%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

The title compound was prepared in 37% yield from N-benzyloxycarbonyl-3-cyclohexylalaninal, ethyl bromodifluoroacetate and zinc by the procedure described in Example 1.

Sources & evidence

ORD record
ord-18c6cc9b63e845c78bbe7780bd05481b
Source dataset
uspto-grants-1992_05
Patent number
US05114927

Reaction notes

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