HCID 178472445, compound → HCID 178463939, compound

HRID 1613489Notes

Reaction equation

HRID 1613489 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]>C(O)C.[OH-].[OH-].[Pd+2]>[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-ethoxycarbonyl-cyclohexyl)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-0817529136e74f1a96c12e31c33d0111
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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