N-(2-phenylethyl)acetamide → Ethyl beta-oxo-beta-[4-(2-acetamidoethyl)-phenyl]-propionate
Reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[Cl-].[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([O-])=[O:17]>>[O:17]=[C:16]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[CH:8][CH:9]=1)[CH2:15][C:14]([O:20][CH2:21][CH3:22])=[O:19]Participants
3
Procedure
N-Acetyl-phenethylamine is reacted with ethyl malonate chloride to give ethyl β-oxo-β-[4-(2-acetamidoethyl)-phenyl]-propionate (m.p. 89°-92° C.), which is reduced to ethyl β-[4-(2-acetamidoethyl)-phenyl]-propionate (m.p. 96°-98° C.) and this then subjected to alkaline saponification to give β-[4-(2-aminoethyl)-phenyl]-propionic acid (m.p. 270°-272° C.) followed by esterification to give the desired ethyl ester hydrochloride.
Sources & evidence
- ORD record
- ord-c1f5cb9f8d734989ba70390943119b4e
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04113871
Reaction notes
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