Hydrochloric Acid → 2-Amino-5,5,5-trifluoropentanoic acid hydrochloride
Reaction equation
C1(C(=[N:14][CH:15]([CH2:23][CH2:24][C:25]([F:28])([F:27])[F:26])[C:16]([O:18]C(C)(C)C)=[O:17])C2C=CC=CC=2)C=CC=CC=1.[ClH:29]>>[ClH:29].[NH2:14][CH:15]([CH2:23][CH2:24][C:25]([F:26])([F:27])[F:28])[C:16]([OH:18])=[O:17]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
A stirred solution of tert-butyl 2-((diphenylmethylene)amino)-5,5,5-trifluoropentanoate (800 mg, 2.023 mmol) in 50% aqueous hydrochloric acid (0.123 mL, 2.023 mmol) was heated to reflux at 100° C. for 8 h. The reaction mixture was cooled to rt and washed with ethyl acetate (10 mL). The aqueous layer was concentrated under reduced pressure to afford 2-amino-5,5,5-trifluoropentanoic acid hydrochloride (400 mg, 1.82 mmol, 90% yield) as white solid. LCMS (ESI) m/e 171.7 [(M+H)+, calcd for C5H7F3O2, 172.1]; LC/MS retention time (method H): tR=0.80 min.
Workup
- temperatureThe reaction mixture was cooled to rt
- washwashed with ethyl acetate (10 mL)
- concentrationThe aqueous layer was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5f4c46b48e36415987411f825a531bd4
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969564B2
Reaction notes
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