Trifluoroacetic acid → 1-((R)-2-amino-3,3-dimethylbutanoyl)-3-fluoropyrrolidine-3-carbonitrile trifluoroacetate

HRID 1898510Notes

Reaction equation

HRID 1898510 reaction equation
[C:1]([C:3]1([F:23])[CH2:7][CH2:6][N:5]([C:8](=[O:22])[C@H:9]([NH:14]C(=O)OC(C)(C)C)[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4]1)#[N:2].[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25]>C(Cl)Cl>[F:27][C:26]([F:29])([F:28])[C:24]([OH:30])=[O:25].[NH2:14][C@H:9]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:8]([N:5]1[CH2:6][CH2:7][C:3]([F:23])([C:1]#[N:2])[CH2:4]1)=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86657871tert-butyl (2R)-1-(3-cyano-3-fluoropyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

Product 1

HCID 673861831-((R)-2-amino-3,3-dimethylbutanoyl)-3-fluoropyrrolidine-3-carbonitrile trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2R)-1-(3-cyano-3-fluoropyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (234 mg, 0.72 mmol) in CH2Cl2 (5 mL) was added TFA (2.0 mL, 26.0 mmol). The reaction mixture was stirred at room temperature for 3 h then concentrated and dried under high vacuum to provide 1-((R)-2-amino-3,3-dimethylbutanoyl)-3-fluoropyrrolidine-3-carbonitrile trifluoroacetate as a pale yellow oil which was used without further purification.

Workup

  1. concentrationthen concentrated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-23410ce97c224bb28a11705b4506e391
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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