Hydrochloric Acid → N-[(1S,3S)-3-aminocyclopentyl]-2,2-difluoro-2-(4-methylphenyl)acetamide

HRID 271392Notes

Reaction equation

HRID 271392 reaction equation
Cl.[F:2][C:3]([F:27])([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)[C:4]([NH:6][C@H:7]1[CH2:11][CH2:10][C@H:9]([NH:12]C(=O)OC(C)(C)C)[CH2:8]1)=[O:5]>CCOC(C)=O>[NH2:12][C@H:9]1[CH2:10][CH2:11][C@H:7]([NH:6][C:4](=[O:5])[C:3]([F:27])([F:2])[C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59834916tert-butyl (1S,3S)-3-{[difluoro(4-methylphenyl)acetyl]amino}cyclopentylcarbamate

Product 1

HCID 59834888N-[(1S,3S)-3-aminocyclopentyl]-2,2-difluoro-2-(4-methylphenyl)acetamideYield 101.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A saturated solution of HCl in EtOAc (10 mL) was added to a stirred solution of tert-butyl (1S,3S)-3-{[difluoro(4-methylphenyl)acetyl]amino}cyclopentylcarbamate (1.05 g, 2.85 mmol) in EtOAc (10 mL). After 1 h the solution was concentrated to dryness. The residue was dissolved in 1:1 CH3CN/H2O (18 mL) and loaded onto SCX ion exchange resin (10 g, 60 mL, 6.9 meq), rinsing with CH3CN (15 mL), and then eluting with EtOH/NH3 (25 mL). The eluent was concentrated to give the title compound (774 mg) as a solid: MS=252.4 (M+1-ammonia).

Workup

  1. concentrationAfter 1 h the solution was concentrated to dryness
  2. dissolutionThe residue was dissolved in 1:1 CH3CN/H2O (18 mL)
  3. washrinsing with CH3CN (15 mL)
  4. washeluting with EtOH/NH3 (25 mL)
  5. concentrationThe eluent was concentrated

Sources & evidence

ORD record
ord-20ee3b2e71e34e11814fb71a093685a5
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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