HCID 178472451, compound → HCID 178472452, compound

HRID 1613490Notes

Reaction equation

HRID 1613490 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH:7]([NH:28]C(OCC1C=CC=CC=1)=O)[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.[Pd]>[C:1]([O:5][C:6](=[O:39])[CH:7]([NH2:28])[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)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 178472451HCID 178472451, compound

Product 1

HCID 178472452HCID 178472452, compoundYield 111.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Benzyloxycarbonylamino-3-{1-[(cis-4-ethoxycarbonylcyclohexyl)carbamoyl]cyclopentyl}-propanoic acid t-butyl ester (8.11 g, 15 mmole) in 10% aqueous ethanol (320 ml) was hydrogenated at 30 p.s.i. (2 bar) for 4 hours over 10% palladium on carbon. The catalyst was removed by filtration and the filtrate evaporated under vacuum. The residue was azeotroped with dichloromethane (3×50 ml) and dried to give the crude title compound as a gum (6.86 g). Rf. 0.6 (silica; methanol, dichloromethane 5:95).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated under vacuum
  3. customThe residue was azeotroped with dichloromethane (3×50 ml)
  4. customdried

Sources & evidence

ORD record
ord-7fe78f32078e43bf862c3c2df6c06218
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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