Ammonia → HCID 22867780, compound

HRID 1080566Notes

Reaction equation

HRID 1080566 reaction equation
Cl[CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH3:16])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[NH3:17]>>[CH2:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C@@H:2]([C:3]([OH:5])=[O:4])[NH2:17])=[CH:8][CH:9]=1)[CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 54053211HCID 54053211, compound

Product 1

HCID 22867780HCID 22867780, compoundYield 46%

Conditions

Temperature
40 °C

Procedure

α-Chloro-β-p-butylphenylpropionic acid 3 (128 g, 0.534 moles) was suspended in 800 mL 30% aqueous ammonia. The reaction was stirred for 4 days at 40° C. in a tightly stoppered flask. After cooling to room temperature, the precipitate was removed by filtration through a coarse glass frit. The solid was washed thoroughly with ethanol followed by diethyl ether. The solid was dried under vacuum yielding 54.3 g (0.245 moles, 46% yield) of p-butylphenylalanine as a white solid. The solid was recrystallized from 2N HCl to give a white solid, mp 218°-223° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe precipitate was removed by filtration through a coarse glass frit
  3. washThe solid was washed thoroughly with ethanol
  4. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-b4e7cf304d054494b45c9ea68f285dd9
Source dataset
uspto-grants-1996_12
Patent number
US05582814

Reaction notes

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