1-Naphthaleneacetic Acid → N-[(1-naphthyl)acetyl]-L-alanine Iso-butyl Ester

HRID 1263898Notes

Reaction equation

HRID 1263898 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[CH2:16]([O:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH2:23])[CH:17]([CH3:19])[CH3:18]>>[CH2:16]([O:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH:23][C:12](=[O:14])[CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH:17]([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 68621-Naphthaleneacetic AcidHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 15481767N-[(1-naphthyl)acetyl]-L-alanine Iso-butyl Ester

Procedure

Following General Procedure BB and using 1-naphthylacetic acid (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example BB above), the title compound was prepared as a solid having a melting point of 69°-73° 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-f383dd572be547cea51f91657091b786
Source dataset
uspto-grants-2003_04
Patent number
US06541466B2

Reaction notes

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