Trifluoroacetic acid → HCID 22291006, compound

HRID 1369512Notes

Reaction equation

HRID 1369512 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:43]=[CH:44][CH:45]=1)[C:20]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:42])=[C:27]([NH:29][C:30](=[O:41])[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)[CH:28]=1)=[O:21])=[O:14])(C)(C)C>C(Cl)Cl>[C:13]([CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:43]=[CH:44][CH:45]=1)[C:20]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:42])=[C:27]([NH:29][C:30](=[O:41])[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)[CH:28]=1)=[O:21])([OH:14])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22291098HCID 22291098, compound

Product 1

HCID 22291006HCID 22291006, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added to a stirred solution of N-[5-(3-tert-butoxycarbonylmethoxybenzamido)-2-methylphenyl]-3,4-dimethoxybenzamide (0.455 g) in methylene chloride (5 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 solid was dried under vacuum at 60° C. There was thus obtained the title compound (0.375 g), m.p. 206-207° C.; NMR Spectrum: (DMSOd6) 2.18 (s, 3H), 3.83 (s, 6H), 4.74 (s, 2H), 7.06 (d, 1H), 7.11 (m, 1H), 7.23 (d, 1H), 7.43 (t, 1H), 7.48 (d, 1H), 7.55 (br m, 1H), 7.63 (m, 1H), 7.8 (d, 1H), 9.75 (br s, 1H), 10.17 (br s, 1H); Mass Spectrum: M+H+ 465.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was azeotroped with toluene
  3. customThe resultant solid was dried under vacuum at 60° C

Sources & evidence

ORD record
ord-5528e66fba9248cd833c1b6d3e70b937
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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