HCID 178472445, compound → HCID 178463939, compound

HRID 1086724Notes

Reaction equation

HRID 1086724 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH:7]([CH2:28][N:29](CC1C=CC=CC=1)[CH2:30][CH3:31])[CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]>[OH-].[OH-].[Pd+2].C(O)C>[C:1]([O:5][C:6](=[O:39])[CH:7]([CH2:28][NH:29][CH2:30][CH3:31])[CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:17][CH2:18][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:21]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178472445HCID 178472445, compound

Product 1

HCID 178463939HCID 178463939, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

2-(N-Benzyl-N-ethylaminomethyl)-3-{1-[(cis-4-ethoxycarbonylcyclohexyl)carbamoyl]cyclopentyl}-propanoic acid t-butyl ester (3.38 g, 6.2 mmole) was dissolved in, ethanol (70 ml) and hydrogenated at 30 p.s.i. (2 bar) over 20% palladium hydroxide on carbon at room temperature for 16 hours. The catalyst was removed by filtration through an Arbacell pad and the filtrate evaporated under vacuum. The residue was chromatographed on silica eluting with methanol-dichloromethane mixtures to give the title compound as an oil (2.35 g, 83%). Found: C,65.51; H,9.57; N,6.14. C25H44N2O5.0.1 CH2Cl2 requires C,65.37; H,9.66; N,6.08%.

Workup

  1. customThe catalyst was removed by filtration through an Arbacell pad
  2. customthe filtrate evaporated under vacuum
  3. customThe residue was chromatographed on silica eluting with methanol-dichloromethane mixtures

Sources & evidence

ORD record
ord-81947a7b83684813b64a1578d5d83581
Source dataset
uspto-grants-1991_07
Patent number
US05030654

Reaction notes

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