Trifluoroacetic acid → N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamide

HRID 1058247Notes

Reaction equation

HRID 1058247 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][CH:32]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[CH:33]([F:35])[F:34])=[C:13]([CH:30]=1)[CH2:14][NH:15][C:16](=[O:29])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1C(OC(C)(C)C)=O>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][CH:32]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[CH:33]([F:35])[F:34])=[C:13]([CH:30]=1)[CH2:14][NH:15][C:16](=[O:29])[C@@H:17]1[CH2:21][CH2:20][CH2:19][NH:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69939378HCID 69939378, compound

Product 1

HCID 69938780N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamideYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5.3 mL) was added to a stirred solution of N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-1-tert-butoxycarbonyl-L-prolinamide (0.626 g, 1.20 mmol) in CH2Cl2 (5.3 mL). After 1 h the solvent was evaporated in vacuo and the residue was partitioned between EtOAc and saturated aqueous Na2CO3. The EtOAc layer was dried (Na2SO4) and evaporated in vacuo to give N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamide (0.439 g) as a foam; MS m/z=438.4.

Workup

  1. customAfter 1 h the solvent was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and saturated aqueous Na2CO3
  3. dry with materialThe EtOAc layer was dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-756ca97785144ad289cbe2e50156ced8
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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