Trifluoroacetic acid → (R)-2-amino-1-(3-fluoro-azetidin-1-yl)-3-methoxy-propan-1-one trifluoroacetate
Reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:16][O:17][CH3:18])[C:9]([N:11]1[CH2:14][CH:13]([F:15])[CH2:12]1)=[O:10])(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]([CH2:16][O:17][CH3:18])[C:9]([N:11]1[CH2:14][CH:13]([F:15])[CH2:12]1)=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 25 mL round-bottomed flask, [(R)-2-(3-fluoro-azetidin-1-yl)-1-methoxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (265 mg, 0.96 mmol) was dissolved in dichloromethane (5 ml). The reaction was cooled to 0° C. and trifluoroacetic acid (1.5 ml, 19.5 mmol) was slowly added. The reaction mixture was stirred at room temperature for 3 h then concentrated to provide (R)-2-amino-1-(3-fluoro-azetidin-1-yl)-3-methoxy-propan-1-one trifluoroacetate as a colorless viscous oil which was used without further purification.
Workup
- concentrationthen concentrated
Sources & evidence
- ORD record
- ord-6a8c9f3b511b4320a8a7679fc19978c0
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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