Trifluoroacetic acid → (R)-2-amino-1-((S)-3-fluoro-pyrrolidin-1-yl)-propan-1-one trifluoroacetate

HRID 246090Notes

Reaction equation

HRID 246090 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH3:17])[C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([F:16])[CH2:12]1)=[O:10])(C)(C)C.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>ClCCl>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[NH2:7][C@H:8]([CH3:17])[C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([F:16])[CH2:12]1)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71279860[(R)-2-((S)-3-fluoropyrrolidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 71280348(R)-2-amino-1-((S)-3-fluoro-pyrrolidin-1-yl)-propan-1-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(R)-2-((S)-3-Fluoro-pyrrolidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (43 mg, 0.127 mmol) was dissolved in dichloromethane (1.6 ml) and cooled in an ice bath. Trifluoroacetic acid (0.8 ml) was slowly added and the reaction was stirred at room temperature for 3 h then evaporated and dried under high vacuum to afford (R)-2-amino-1-((S)-3-fluoro-pyrrolidin-1-yl)-propan-1-one trifluoroacetate which was used without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customthen evaporated
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-a9ca333576004d9e87ae8db7e29043a4
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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