Trifluoroacetic acid → 1-((R)-2-amino-3,3-dimethyl-butyryl)-azetidine-3-carbonitrile trifluoroacetate

HRID 245880Notes

Reaction equation

HRID 245880 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:13]([N:15]1[CH2:18][CH:17]([C:19]#[N:20])[CH2:16]1)=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C.[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25]>ClCCl>[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25].[NH2:7][C@H:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:13]([N:15]1[CH2:16][CH:17]([C:19]#[N:20])[CH2:18]1)=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71279421[(R)-1-(3-cyano-azetidine-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 712804851-((R)-2-amino-3,3-dimethyl-butyryl)-azetidine-3-carbonitrile trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution [(R)-1-(3-cyano-azetidine-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester (180 mg, 0.49 mmol) in dichloromethane (3 ml) at 0° C. was added trifluoroacetic acid (1.2 ml, 15.6 mmol). The reaction mixture was stirred at room temperature for 2 h then concentrated to afford 1-((R)-2-amino-3,3-dimethyl-butyryl)-azetidine-3-carbonitrile trifluoroacetate as a light yellow oil which was used without further purification.

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-15349e66bdea48d9b80b4883e75bc213
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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