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

HRID 986774

Reaction equation

HRID 986774 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-18d49c616b4e489b9d2506c44a303e72
Source dataset
uspto-grants-1987_12
Patent number
US04716155

Linked notes

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