Trifluoroacetic acid → Trifluoroacetic acid

HRID 967883Notes

Reaction equation

HRID 967883 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-butoxycarbonylmethoxybenzamide (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-1f02d692f1574057aa712c07d01dc537
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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