N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanine → N-[N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-L-phenylalanyl]-3-mercapto-D-valine, methyl ester

HRID 1586891Notes

Reaction equation

HRID 1586891 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:22][O:23][C:24](=[O:31])[C@@H:25]([C:27]([SH:30])([CH3:29])[CH3:28])[NH2:26]>>[CH3:7][C:4]([CH3:5])([O:3][C:1]([NH:8][C@H:9]([C:18]([NH:26][C@@H:25]([C:24]([O:23][CH3:22])=[O:31])[C:27]([SH:30])([CH3:29])[CH3:28])=[O:20])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)=[O:2])[CH3:6]

Participants

3

Reactant 2

HCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanineHCID 12278508Methyl 3-mercapto-D-valinate hydrochloride

Product 1

HCID 131717964N-[N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-L-phenylalanyl]-3-mercapto-D-valine, methyl ester

Procedure

The title compound was synthesized by coupling Nα -Boc-(p-fluoro) phenylalanine (1.3 g, 40.0 mmol) to 8.2 g (41.0 mmol) of D-penicillamine methylester hydrochloride using the procedure described above in Example 19. The title compound was obtained as a white solid (14.8 g, 86.5%).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-c3de961e76bb4d21a60d7a23ae756953
Source dataset
uspto-grants-1993_06
Patent number
US05216124

Reaction notes

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