HCID 178496223, compound → HCID 178496222, compound

HRID 1613502Notes

Reaction equation

HRID 1613502 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]([C@H:13]([CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])[CH2:14][C:15]3([C:20]([NH:22][C@@H:23]4[CH2:28][CH2:27][C@H:26]([C:29]([O:31]CC5C=CC=CC=5)=[O:30])[CH2:25][CH2:24]4)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>C(O)C.[Pd]>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]([C@H:13]([CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])[CH2:14][C:15]3([C:20]([NH:22][C@@H:23]4[CH2:24][CH2:25][C@H:26]([C:29]([OH:31])=[O:30])[CH2:27][CH2:28]4)=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19]3)=[O:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 178496223HCID 178496223, compound

Product 1

HCID 178496222HCID 178496222, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-benzyl cis-4-{1-[2-(5-indanyloxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxamido}-1-cyclohexanecarboxylate (597 mg, 0.986 mmole) in 5% aqueous ethanol (10 ml) was hydrogenated over 10% palladium on charcoal catalyst (60 mg) at 60 p.s.i. (4.1 bar) and room temperature for 3.5 hours. The catalyst was removed by filtration and the filtrate evaporated under vacuum. The residue was dissolved in diethyl ether (50 ml) and the solution was clarified by filtration, and concentrated to low volume (about 5 ml) when crystallisation occurred. After granulation, filtration and drying gave the title ester (390 mg, 77%) as white crystals m.p. 107°-9° C., [α]D -5.8° (c=1, MeOH), Rf. 0.40 (silica; toluene, dioxane, acetic acid 90:24:5). Found: C,67.45; H,8.18; N,2.63. C29H41NO7 requires C,67.55; H,8.01; N,2.72%.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated under vacuum
  3. dissolutionThe residue was dissolved in diethyl ether (50 ml)
  4. filtrationthe solution was clarified by filtration
  5. concentrationconcentrated to low volume (about 5 ml) when crystallisation
  6. filtrationAfter granulation, filtration
  7. customdrying

Sources & evidence

ORD record
ord-35338a5c5f5a4d17970bda63da97adcb
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

Loading…