Trifluoroacetic acid → Trifluoroacetic acid

HRID 1369522Notes

Reaction equation

HRID 1369522 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][N:9]([CH3:44])[C:10]1[CH:11]=[C:12]([CH:41]=[CH:42][CH:43]=1)[C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:40])=[C:20]([NH:22][C:23](=[O:39])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32]([O:34]C(C)(C)C)=[O:33])[CH:25]=2)[CH:21]=1)=[O:14]>C(Cl)Cl>[CH3:44][N:9]([CH3:8])[C:10]1[CH:11]=[C:12]([CH:41]=[CH:42][CH:43]=1)[C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:40])=[C:20]([NH:22][C:23](=[O:39])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32]([OH:34])=[O:33])[CH:25]=2)[CH:21]=1)=[O:14].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22291026HCID 22291026, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 22291131HCID 22291131, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to a stirred solution of N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]-3-tert-butoxycarbonylmethoxy-benzamide (0.5 g) in methylene chloride (10 ml) and the mixture was stirred at ambient temperature for 1 hour. The mixture was evaporated and the residue was azeotroped with toluene. The resultant gum was triturated under diethyl ether. The solid so obtained was isolated and dried under vacuum at 60° C. There was thus obtained the title compound as its trifluoroacetic acid salt (0.39 g); NMR Spectrum: (DMSOd6) 2.17 (s, 3H), 2.93 (s, 6H), 4.76 (s, 2H), 6.93 (m, 1H), 7.13 (m, 1H), 7.23 (m, 3H), 7.3 (t, 1H), 7.43 (t, 1H), 7.51 (d, 1H), 7.59 (d, 2H), 7.78 (d, 1H), 9.88 (br s, 1H), 10.1 (br s, 1H); Mass Spectrum: M−H− 446.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was azeotroped with toluene
  3. customThe resultant gum was triturated under diethyl ether
  4. customThe solid so obtained
  5. customwas isolated
  6. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-3201ce0c013f4624a07b6b23faa0bb98
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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