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

HRID 1859111Notes

Reaction equation

HRID 1859111 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.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:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[CH:17]([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 113932-Naphthaleneacetic acidHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

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

Procedure

Following General Procedure B' and using 2-naphthylacetic acid (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example B' 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.

Sources & evidence

ORD record
ord-34a2f42c35254496966d9b41b3d72134
Source dataset
uspto-grants-2000_11
Patent number
US06153652

Reaction notes

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