HCID 11809525, compound → HCID 10914471, compound

HRID 1251410Notes

Reaction equation

HRID 1251410 reaction equation
[OH:1][NH:2][C:3](=[O:22])[C:4]([CH2:19][CH:20]=[CH2:21])([S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH2:5][CH:6]=[CH2:7]>CO.[Pd]>[OH:1][NH:2][C:3](=[O:22])[C:4]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=[O:9])=[O:10])([CH2:19][CH2:20][CH3:21])[CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 11809525HCID 11809525, compound

Product 1

HCID 10914471HCID 10914471, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-allyl-2-(4-methoxy-benzenesulfonyl)-pent-4-enoic acid hydroxyamide (326 mg, 1.0 mmol), (example 26) was dissolved in methanol (50 ml) and hydrogenated over 10% Pd/C (100 mg) at room temperature, under 49 psi pressure for 4 hours. At the end, the reaction mixture was filtered and methanol was removed. The resulting solid was crystallized from methanol. Yield: 250 mg, 75%; MS: 330 (M+H)+; 1H NMR (300 MHz, CDCl3): δ0.92 (t, J=4.0 Hz, 6H), 1.27-1.59 (m, 4H), 1.78-2.02 (m, 4H), 3.86 (s, 3H), 6.04 (bs, 1H), 6.97 (d, J=9 Hz, 2H), 7.76 (d,J=9 Hz, 2H).

Workup

  1. filtrationAt the end, the reaction mixture was filtered
  2. custommethanol was removed
  3. customThe resulting solid was crystallized from methanol

Sources & evidence

ORD record
ord-8d9d4cd2da464d2faadf669a265bfe09
Source dataset
uspto-grants-2002_01
Patent number
US06342508B1

Reaction notes

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