Methyl L-phenylalaninate hydrochloride → N-benzyloxycarbonyl (beta-benzyl)-L-aspartyl-L-phenylalanine methyl ester

HRID 1764432Notes

Reaction equation

HRID 1764432 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:24](O)=[O:25])[CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:28][O:29][C:30](=[O:40])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH2:32]>CN(C)C=O>[CH3:28][O:29][C:30](=[O:40])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH:32][C:24](=[O:25])[C@H:12]([CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14](=[O:15])[OH:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

4

Reactant 2

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 18324139N-benzyloxycarbonyl-(beta-benzyl)-D,L-aspartic acid

Product 1

HCID 14876780N-benzyloxycarbonyl (beta-benzyl)-L-aspartyl-L-phenylalanine methyl esterYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The process of Example 50 was repeated except that 715 mg (2.00 mmol) of N-benzyloxycarbonyl-(β-benzyl)-D,L-aspartic acid and 215 mg of L-phenylalanine methyl ester hydrochloride, 200 mg of Prolisin and 200 mg of the inhibitor were reacted. As a result, an 110 mg amount (yield of 21.2%) of N-benzyloxycarbonyl-(β-benzyl)-L-aspartyl-L-phenylalanine methyl ester having an [α]D22 = -12.8 (C-1.0 dimethylformamide) was obtained.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a06e61057c8743539117e1cad29c7917
Source dataset
uspto-grants-1978_09
Patent number
US04116768

Reaction notes

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