Trifluoroacetic acid → 1-((R)-2-amino-3-methoxy-propionyl)-azetidine-3-carbonitrile trifluoroacetate
Reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:17][O:18][CH3:19])[C:9]([N:11]1[CH2:14][CH:13]([C:15]#[N:16])[CH2:12]1)=[O:10])(C)(C)C.[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24]>ClCCl>[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24].[NH2:7][C@H:8]([CH2:17][O:18][CH3:19])[C:9]([N:11]1[CH2:14][CH:13]([C:15]#[N:16])[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-cyano-azetidin-1-yl)-1-methoxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (286 mg, 1.00 mmol) was dissolved in dichloromethane (4 ml). The reaction was cooled to 0° C. and trifluoroacetic acid (1.2 ml, 15.6 mmol) was slowly added. The reaction mixture was stirred at room temperature for 3 h then concentrated to provide 1-((R)-2-amino-3-methoxy-propionyl)-azetidine-3-carbonitrile trifluoroacetate as a colorless viscous oil which was used without further purification.
Workup
- concentrationthen concentrated
Sources & evidence
- ORD record
- ord-7dfacb3eaa9445d8ba847f16be5125f4
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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