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

HRID 245830Notes

Reaction equation

HRID 245830 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:11]([N:13]1[CH2:16][CH:15]([C:17]#[N:18])[CH2:14]1)=[O:12])[CH2:9][CH3:10])(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]([CH2:9][CH3:10])[C:11]([N:13]1[CH2:14][CH:15]([C:17]#[N:18])[CH2:16]1)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71280211[(R)-1-(3-cyano-azetidine-1-carbonyl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 712804521-((R)-2-amino-butyryl)-azetidine-3-carbonitrile trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(R)-1-(3-cyano-azetidine-1-carbonyl)-propyl]-carbamic acid tert-butyl ester (200 mg, 0.67 mmol) in dichloromethane (4 ml) was added trifluoroacetic acid (1.8 ml, 23.4 mmol). The reaction mixture was stirred at room temperature for 2 h then concentrated to afford 1-((R)-2-amino-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-c4c140987710465fb9bf86b8190d9bb8
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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