tert-Butyl [(S)-1-(1-cyanocyclopropylcarbamoyl)-3,3-difluorobutyl]carbamate → N-(1-cyanocyclopropyl)-(S)-2-amino-4,4-difluoropentanamide

HRID 1913324Notes

Reaction equation

HRID 1913324 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]([NH:15]C(=O)OC(C)(C)C)[CH2:10][C:11]([F:14])([F:13])[CH3:12])=[O:8])[CH2:5][CH2:4]1)#[N:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:1]([C:3]1([NH:6][C:7](=[O:8])[C@@H:9]([NH2:15])[CH2:10][C:11]([F:14])([F:13])[CH3:12])[CH2:4][CH2:5]1)#[N:2]

Participants

3

Reactant 1

HCID 68974749tert-Butyl [(S)-1-(1-cyanocyclopropylcarbamoyl)-3,3-difluorobutyl]carbamate

Product 1

HCID 66661333N-(1-cyanocyclopropyl)-(S)-2-amino-4,4-difluoropentanamide

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To detach the Boc protecting group, the compound from example 17 (580 mg, 1.83 mmol) was admixed with 10 ml of 1:1 TFA/DCM and stirred at RT for 30 min. Subsequently, the mixture was concentrated by evaporation under reduced pressure and subjected to azeotropic distillation with dichloromethane and toluene, and solvent residues were removed under high vacuum. The product was present as the trifluoroaceate.

Workup

  1. concentrationSubsequently, the mixture was concentrated by evaporation under reduced pressure
  2. distillationsubjected to azeotropic distillation with dichloromethane and toluene, and solvent residues
  3. customwere removed under high vacuum

Sources & evidence

ORD record
ord-d964dcafff90418d99b4bb40eff7e039
Source dataset
uspto-grants-2013_12
Patent number
US08609681B2

Reaction notes

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