Boc-N-Me-Phe-OH → N-[N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-L-phenylalanyl]-3-mercapto-D-valine, methyl ester

HRID 1586890Notes

Reaction equation

HRID 1586890 reaction equation
[C:1]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[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]([N:8]([CH3:20])[C@H:9]([C:17]([NH:26][C@@H:25]([C:24]([O:23][CH3:22])=[O:31])[C:27]([SH:30])([CH3:29])[CH3:28])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:2])[CH3:6]

Participants

3

Reactant 2

HCID 7010602Boc-N-Me-Phe-OHHCID 12278508Methyl 3-mercapto-D-valinate hydrochloride

Product 1

HCID 131717963N-[N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-L-phenylalanyl]-3-mercapto-D-valine, methyl ester

Procedure

The title compound was synthesized by coupling Nα -Boc-(N-methyl) phenylalanine (19.0 g, 68.0 mmol) to 13.8 g (69.0 mmol) of D-penicillamine methylester hydrochloride using the procedure described above in Example 19. The title compound was obtained as a white solid (29.6 g, 99.3%).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-44e0de502cb64c53ab633e36161e2ce3
Source dataset
uspto-grants-1993_06
Patent number
US05216124

Reaction notes

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