Hydrochloric Acid → 2-Amino-4-phenylbutyrate ethyl hydrochloride

HRID 1583948

Reaction equation

HRID 1583948 reaction equation
[NH2:1][CH:2]([C:11]([OH:13])=[O:12])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[ClH:14].[CH2:15](O)[CH3:16]>>[ClH:14].[NH2:1][CH:2]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:11]([O:13][CH2:15][CH3:16])=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 102530Homophenylalanine, DL-

Product 1

HCID 533952832-Amino-4-phenylbutyrate ethyl hydrochloride

Procedure

A suspension of d,l-homophenylalanine (5 g., 27.9 mmole) in absolute ethanol (60 ml.) was cooled to 0° (ice bath) and saturated with hydrochloric acid gas. The mixture was allowed to warm to room temperature and stirred overnight. A stream of nitrogen was then passed through the solution to remove the bulk of the hydrochloric acid and the mixture was evaporated to dryness. The solid residue was triturated with ether, filtered and dried to give (±)-α-aminobenzenebutanoic acid, ethyl ester, monohydrochloride as a fluffy white solid; m.p. 129°-130°. Rf (acetic acid/methanol/dichloromethane; 1:1:8)=0.63.

Workup

  1. temperaturewas cooled to 0° (ice bath)
  2. customto remove the bulk of the hydrochloric acid
  3. customthe mixture was evaporated to dryness
  4. customThe solid residue was triturated with ether
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-b4b9aae2b2e54730a8980873ba7da2f8
Source dataset
uspto-grants-1985_11
Patent number
US04555506

Linked notes

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