HCID 17897280, compound → HCID 10914471, compound

HRID 1595597Notes

Reaction equation

HRID 1595597 reaction equation
[OH:1][NH:2][C:3](=[O:42])[C:4]([S:31]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)(=[O:33])=[O:32])([CH2:15][C:16]1C=CC(OCCN2CCOCC2)=C[CH:17]=1)[CH2:5]/[CH:6]=[C:7](\C)/CCC=C(C)C>CO.[Pd]>[OH:1][NH:2][C:3](=[O:42])[C:4]([S:31]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)(=[O:32])=[O:33])([CH2:15][CH2:16][CH3:17])[CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 17897280HCID 17897280, 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)30 ; 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-40a02caa611e4cfab5889fe10fd35166
Source dataset
uspto-grants-2001_09
Patent number
US06288086B1

Reaction notes

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