HCID 10746110, compound → HCID 11799762, compound

HRID 1645791Notes

Reaction equation

HRID 1645791 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[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]>[CH2:41]([O:40][C:38]([CH2:37][N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[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:39])[CH3:42]

Participants

4

Reactant 1

HCID 10746110HCID 10746110, compound

Product 1

HCID 11799762HCID 11799762, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl 4-[N,N-bis(ethoxycarbonylmethyl)carbamoyl]-5-(2-naphthylsulfonyl)pentanoate (0.52 g) in ethanol (10 ml) was added 10% Pd-C (50 mg), and the mixture was hydrogenolyzed at atmospheric pressure and ambient temperature for 4 days. After the catalyst was filtered off, the filtrate was evaporated at reduced pressure. The residue was purified by flash column chromatography on silica eluting with chloroform/methanol (10:1), and recrystallized from isopropyl ether-hexane to give 0.27 g of 4-[N,N-bis(ethoxycarbonylmethyl)carbamoyl]-5-(2-naphthylsulfonyl)pentanoic acid.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. customthe filtrate was evaporated at reduced pressure
  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-6d67b8bad10b4ede828c09ff60dc06e4
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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