HCID 21997034, compound → HCID 21997015, compound

HRID 1457350Notes

Reaction equation

HRID 1457350 reaction equation
C([O:8][NH:9][C:10](=[O:38])[CH:11]([CH2:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH2:12][CH2:13][CH2:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C>[OH:8][NH:9][C:10](=[O:38])[CH:11]([CH2:26][S:27]([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)(=[O:29])=[O:28])[CH2:12][CH2:13][CH2:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)(=[O:16])=[O:17]

Participants

4

Reactant 1

HCID 21997034HCID 21997034, compound

Product 1

HCID 21997015HCID 21997015, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-benzyloxy-2-[(4-methoxybenzenesulfonyl)methyl]-5-(4-methoxybenzenesulfonyl)-pentanamide (0.3 g, 0.5 mmol), Pearlman's catalyst (0.11 g), and absolute ethyl alcohol is agitated under hydrogen (15 psig) overnight at room temperature. The mixture is filtered and the filtrate is concentrated in vacuo. The concentrate is chromatographed over silica gel with chloroform/ethyl acetate/methyl alcohol/acetic acid (50/40/10/1) and the eluate concentrated in vacuo to afford the title compound as a white solid.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe concentrate is chromatographed over silica gel with chloroform/ethyl acetate/methyl alcohol/acetic acid (50/40/10/1)
  4. concentrationthe eluate concentrated in vacuo

Sources & evidence

ORD record
ord-8154d9319bd5422caaa476cfb5052e58
Source dataset
uspto-grants-1998_12
Patent number
US05847153

Reaction notes

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