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

HRID 246101Notes

Reaction equation

HRID 246101 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-cyanoazetidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (47 mg, 0.185 mmol) was dissolved in dichloromethane (1 ml) and cooled in an ice bath. Trifluoroacetic acid (0.5 ml) was slowly added and the reaction was stirred at room temperature for 2 h then evaporated and dried under high vacuum to afford 1-((R)-2-amino-propionyl)-azetidine-3-carbonitrile 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-75e169a338254f73aa75681bbc65fe9a
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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