Trifluoroacetic acid → (R)-2-amino-1-(3-fluoro-azetidin-1-yl)-pentan-1-one trifluoroacetate

HRID 245924Notes

Reaction equation

HRID 245924 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:12]([N:14]1[CH2:17][CH:16]([F:18])[CH2:15]1)=[O:13])[CH2:9][CH2:10][CH3:11])(C)(C)C.[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23]>ClCCl>[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].[NH2:7][C@H:8]([CH2:9][CH2:10][CH3:11])[C:12]([N:14]1[CH2:15][CH:16]([F:18])[CH2:17]1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71279341[(R)-1-(3-fluoro-azetidine-1-carbonyl)-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 71280296(R)-2-amino-1-(3-fluoro-azetidin-1-yl)-pentan-1-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round-bottomed flask, [(R)-1-(3-fluoro-azetidine-1-carbonyl)-butyl]-carbamic acid tert-butyl ester (200 mg, 0.66 mmol) was dissolved in dichloromethane (4 ml) and trifluoroacetic acid (1.6 ml, 20.8 mmol) was slowly added. The reaction mixture was stirred at room temperature for 2 h then concentrated to provide (R)-2-amino-1-(3-fluoro-azetidin-1-yl)-pentan-1-one trifluoroacetate as a pale brown oil which was used without further purification.

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-6b9041faf35842779898fdbf54679cdb
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…