Trifluoroacetic acid → HCID 18672430, compound

HRID 1058245Notes

Reaction equation

HRID 1058245 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:24][CH:25]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[CH:26]([F:28])[F:27])=[C:13]([CH:23]=1)[CH2:14][NH:15]C(=O)OC(C)(C)C>C(Cl)Cl>[NH2:15][CH2:14][C:13]1[CH:23]=[C:9]([Cl:8])[CH:10]=[CH:11][C:12]=1[CH2:24][CH:25]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[CH:26]([F:28])[F:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18672390Tert-butyl 5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzylcarbamate

Product 1

HCID 18672430HCID 18672430, compoundYield 137.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5.2 mL) was added to a stirred solution of tert-butyl 5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzylcarbamate (0.516 g, 1.17 mmol) in CH2Cl2 (5.2 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-{1-[2-(aminomethyl)-4-chlorobenzyl]-2,2-difluoroethyl}-N-(4-methoxyphenyl)amine (0.550 g) as a foam; MS m/z=341.1.

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-559c9629af0944898513ffd5bd931211
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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