Hydrochloric Acid → 2-Amino-5,5,5-trifluoropentanoic acid hydrochloride

HRID 1398330Notes

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

Reactant 2

HCID 313Hydrochloric Acid

HCID 86695928HCID 86695928, compound

Product 1

HCID 717585042-Amino-5,5,5-trifluoropentanoic acid hydrochlorideYield 90%

Procedure

A stirred solution of tert-butyl 2-((diphenylmethylene)amino)-5,5,5-trifluoropentanoate (800 mg, 2.023 mmol) in 50% aqueous HCl (0.123 mL, 2.023 mmol) was refluxed at 100° C. for 8 h. The reaction mixture was cooled to rt and concentrated under reduced pressure to afford 2-amino-5,5,5-trifluoropentanoic acid hydrochloride (400 mg, 1.82 mmol, 90% yield, 78% pure by LC/MS) as a white solid. LC/MS (ESI) m/e 171.7 [(M+H)+, calcd for C5H7F3O2, 172.1]; LC/MS retention time (method E): tR=0.80 min.

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-243a7607eeea47f6b0d3a96e41cb4072
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901305B2

Reaction notes

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