L-Alanine → N-[(2-naphthyl)acetyl]-L-alanine Iso-butyl Ester

HRID 133358Notes

Reaction equation

HRID 133358 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([OH:14])=O.[NH2:15][C@H:16]([C:18]([OH:20])=[O:19])[CH3:17]>>[CH2:1]([O:19][C:18](=[O:20])[C@H:16]([CH3:17])[NH:15][C:12](=[O:14])[CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[CH:2]([CH3:11])[CH3:3]

Participants

3

Reactant 2

HCID 5950L-AlanineHCID 113932-Naphthaleneacetic acid

Product 1

HCID 15481768N-[(2-naphthyl)acetyl]-L-alanine Iso-butyl Ester

Procedure

Following General Procedure BB and using 2-naphthylacetic acid (Aldrich) and L-alanine is iso-butyl ester hydrochloride (from Example BB above), the title compound was prepared as a solid having a melting point of 128°-129° C. The reaction was monitored by tlc on silica gel and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl.

Workup

  1. customThe reaction was monitored by tlc on silica gel and purification
  2. extractionwas by extraction with Et2O

Sources & evidence

ORD record
ord-b6ffa61a8c7b4a9cb5f26d2206c05357
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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