(4-{[Benzyl({[3,5-bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl phenylcarbamate → (4-{[({[3,5-Bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl phenylcarbamate

HRID 23731Notes

Reaction equation

HRID 23731 reaction equation
[C:1]1([NH:7][C:8](=[O:46])[O:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][N:18](CC3C=CC=CC=3)[S:19]([NH:22][C:23](=[O:38])[C:24]3[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=3)(=[O:21])=[O:20])[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]1([NH:7][C:8](=[O:46])[O:9][CH2:10][CH:11]2[CH2:12][CH2:13][CH:14]([CH2:17][NH:18][S:19]([NH:22][C:23](=[O:38])[C:24]3[CH:29]=[C:28]([C:30]([F:32])([F:31])[F:33])[CH:27]=[C:26]([C:34]([F:35])([F:36])[F:37])[CH:25]=3)(=[O:20])=[O:21])[CH2:15][CH2:16]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 22574466(4-{[Benzyl({[3,5-bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl phenylcarbamate

Product 1

HCID 22574490(4-{[({[3,5-Bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl phenylcarbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

7 (31.5 mg, 47 mmole, 1.0 eq) was dissolved in 4/1 methanol/ethyl acetate (1.25 mL) and 15 mg of 20% palladium hydroxide on carbon (wet) was added. The vessel was evacuated and charged with hydrogen and stirred overnight. The catalyst was fitered over celite and the filtrate evaporated to give the title compound in nearly quantitative yield. 1H NMR (500 MHz, DMSO-d6): δ 12.23 (br s, 1H), 9.54 (s, 1H), 8.50 (s, 2H), 8.28 (s, 1H), 7.42 (d, 2H), 7.24 (t, 2H), 6.95 (t, 1H), 3.84 (d, 2H), 2.70 (br s, 2H), 1.54-1.38 (m, 2H), 0.88 (m, 4H).

Workup

  1. additionwas added
  2. customThe vessel was evacuated
  3. additioncharged with hydrogen
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-ccb3f757053e4e919cb68765113bad58
Source dataset
uspto-grants-2005_02
Patent number
US06852738B2

Reaction notes

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