Cyclohexene → HCID 86752398, compound

HRID 1598920Notes

Reaction equation

HRID 1598920 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]([CH2:22][C:23](=[O:49])[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]([CH:33]1[CH2:38][CH2:37][N:36](C(OCC2C=CC=CC=2)=O)[CH2:35][CH2:34]1)=[O:32])[C:10](=[O:21])[NH:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCCCC=1>C(O)C.[C].[Pd]>[C:1]([O:5][C:6]([CH2:8][N:9]([CH2:22][C:23](=[O:49])[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]([CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)=[O:32])[C:10](=[O:21])[NH:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 86752399HCID 86752399, compound2×

Product 1

HCID 86752398HCID 86752398, compoundYield 1,495.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(3-(tert-butoxycarbonylmethyl(2-(N-(benzyloxycarbonyl)piperidine-4-carbonyl)phenylcarbamoylmethyl)ureido)benzoic acid (compound 53) (19 mg, 1.49 μmol) in ethanol (1.0 ml) are added cyclohexene (144 μl) and 10% palladium-carbon (15 mg), and the mixture is refluxed with stirring for 30 minutes. The reaction solution is filtered and the filtrate is concentrated under reduced pressure to obtain the titled compound 54 (12 mg). Yield 79%.

Workup

  1. temperaturethe mixture is refluxed
  2. filtrationThe reaction solution is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ba33befeb2e142d3a5b22198b76d3e62
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

Loading…