5-Ethoxy-1,3-dihydro-(2-methoxy-4-benzyloxycarbonylbenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one → 5-Ethoxy-1,3-dihydro-1-(2-methoxy-4-carboxybenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one

HRID 1081486Notes

Reaction equation

HRID 1081486 reaction equation
[CH2:1]([O:3][C:4]1[CH:40]=[CH:39][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29]CC4C=CC=CC=4)=[O:28])=[CH:23][C:22]=3[O:37][CH3:38])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]1[CH:40]=[CH:39][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][C:22]=3[O:37][CH3:38])(=[O:19])=[O:20])[C:9](=[O:17])[N:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[C:6]=2[CH:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 152315525-Ethoxy-1,3-dihydro-(2-methoxy-4-benzyloxycarbonylbenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one

Product 1

HCID 152290425-Ethoxy-1,3-dihydro-1-(2-methoxy-4-carboxybenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-oneYield 73.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4 g of 5-ethoxy-1,3-dihydro-1-(2-methoxy-4-benzyloxycarbonylbenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one in 100 ml of AcOEt were hydrogenated at room temperature and at atmospheric pressure in the presence of 200 mg of Pd/C. The catalyst was filtered off on C elite® and the filtrate was concentrated under vacuum. 2.47 g of the expected compound were obtained in the form of a white solid by crystallization from iso ether. M.p.=205° C.

Workup

  1. filtrationThe catalyst was filtered off on C elite®
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-88b330ce73f84efdb7d0726e49902d67
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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