Trifluoroacetic acid → 1-((R)-2-amino-propionyl)-azetidine-3-carbonitrile trifluoroacetate

HRID 1898505Notes

Reaction equation

HRID 1898505 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH3:17])[C:9]([N:11]1[CH2:14][CH:13]([C:15]#[N: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[CH2:12][CH:13]([C:15]#[N:16])[CH2:14]1)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67386290HCID 67386290, compound

Product 1

HCID 673864061-((R)-2-amino-propionyl)-azetidine-3-carbonitrile trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(R)-2-(3-Cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (1.05 g, 3.27 mmol) was dissolved in 4 mL of dichloromethane. The solution was cooled in an ice bath and 1.2 mL of trifluoroacetic acid was added slowly. After 1.5 h the reaction was concentrated to afford 1-((R)-2-amino-propionyl)-azetidine-3-carbonitrile trifluoroacetate which was used without further purification.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. concentrationAfter 1.5 h the reaction was concentrated

Sources & evidence

ORD record
ord-08d41d22e4da4be3b672555463ccb142
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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