HCID 10698488, compound → HCID 10767422, compound

HRID 1645793Notes

Reaction equation

HRID 1645793 reaction equation
[C:1]([O:4][CH2:5][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:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([O:4][CH2:5][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:25])=[O:26])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 10698488HCID 10698488, compound

Product 1

HCID 10767422HCID 10767422, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of benzyl 4-[N-(2-acetoxyethyl)-N-pentylcarbamoyl]-5-(2-naphthylsulfonyl)pentanoate (0.40 g) in acetic acid (5 ml) was added 10% Pd-C (0.05 g), and the mixture was hydrogenolyzed at atmospheric pressure and ambient temperature for 48 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) to give 0.16 g of 4-[N-(2-acetoxyethyl)-N-pentylcarbamoyl]-5-(2-naphthylsulfonyl)pentanoic acid as oil. ##STR28##

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)

Sources & evidence

ORD record
ord-5cd663eff9794380adb20f5908d20524
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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