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

HRID 1664714Notes

Reaction equation

HRID 1664714 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-1eac99ec42b745c580f1c49079bac958
Source dataset
uspto-grants-2011_10
Patent number
US08039480B2

Reaction notes

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