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

HRID 1841139Notes

Reaction equation

HRID 1841139 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-8284690faf3647ef88693e8f259af8b7
Source dataset
uspto-grants-2004_01
Patent number
US06683075B1

Reaction notes

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