HCID 10531324, compound → HCID 10601170, compound

HRID 1645788Notes

Reaction equation

HRID 1645788 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:8]([CH:10]([CH2:23][S:24]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)(=[O:26])=[O:25])[CH2:11][CH2:12][C:13]([O:15]CC1C=CC=CC=1)=[O:14])=[O:9])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][N:7]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:8]([CH:10]([CH2:23][S:24]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)(=[O:26])=[O:25])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:9])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 10531324HCID 10531324, compound

Product 1

HCID 10601170HCID 10601170, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl 4-(N-ethoxycarbonylmethyl-N-pentylcarbamoyl)-5-(2-naphthylsulfonyl)pentanoate (200 mg) in ethanol (10 ml) was added 10% Pd-C (20 mg), and the mixture was hydrogenolyzed at atmospheric pressure for 60 hours. After the catalyst was filtered off, the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica eluting with chloroform/methanol (10:1), and recrystallized from isopropyl ether-hexane to give 170 mg of 4-(N-ethoxycarbonylmethyl-N-pentylcarbamoyl)-5-(2-naphthylsulfonyl)pentanoic acid.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica eluting with chloroform/methanol (10:1)
  4. customrecrystallized from isopropyl ether-hexane

Sources & evidence

ORD record
ord-897c05ab624b4dd7992b634a1b4cf5f4
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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