Benzaldehyde → HCID 67869983, compound

HRID 2081185Notes

Reaction equation

HRID 2081185 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C(Br)C1C=CC=CC=1>>[CH3:1][O:2][C:3](=[O:13])[C@H:4]([CH2:6][C:7]1([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH2:8]1)[NH2:5]

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 7498Benzyl BromideHCID 736234L-Phenylalanine, methyl esterHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 67869983HCID 67869983, compound

Procedure

The synthesis of the benzylphenylalanine methyl ester is described in Scheme II-29. The imine is formed by treating phenylalanine methyl ester with benzaldehyde followed by deprotonation with lithium hexamethyldisilazide to generate the anion and alkylation with benzylbromide to give 1-benzylphenylalanine methyl ester 115. ##STR38##

Sources & evidence

ORD record
ord-6ebb698691ae4409b17a4ccc3138523f
Source dataset
uspto-grants-1993_02
Patent number
US05183810

Reaction notes

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