HCID 21997034, compound → HCID 21997015, compound

HRID 1978223Notes

Reaction equation

HRID 1978223 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 mitue 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 mitue 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-3e0356cdd77c431e9a53322c94847c3b
Source dataset
uspto-grants-2001_05
Patent number
US06235928B1

Reaction notes

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