Ethanol → HCID 18790065, compound

HRID 1107117Notes

Reaction equation

HRID 1107117 reaction equation
C(ON[C:10](=[O:36])[CH2:11][C:12]([S:25]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)(=[O:27])=[O:26])([CH2:23][CH3:24])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C1C=CC=CC=1.CC[OH:39]>[Pd]>[CH3:35][O:34][C:31]1[CH:30]=[CH:29][C:28]([S:25]([C:12]([CH2:23][CH3:24])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][C:10]([OH:39])=[O:36])(=[O:26])=[O:27])=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 18790164HCID 18790164, compound

Product 1

HCID 18790065HCID 18790065, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 0.463 g (0.91 mmol) of N-benzyloxy-3-(4-methoxyphenylsulfonyl)-3-ethyl-7-phenylheptanamide in 75 mL of EtOH is shaken for 3 days under 50 psi of H2 with 0.2 g of 10% Pd on carbon. The mixture is filtered and concentrated in vacuo. Purification by flash silica gel chromatography afforded 0.1 g (26%) of 3-(4-methoxybenzenesulfonyl)-3-ethyl-7-phenylheptanoic acid hydroxamide in the form of a white foam, m.p. 44-46° C.1H NMR (DMSO-d6) δ (TMS)0.97 (t, 3H), 1.45-1.9 (m, 8H), 2.4 (s, 2H), 2.55 (m, 2H), 3.87 (s, 3H), 7.1-7.25(m, 5H), 7.28 (d, 2H), 7.65 (d, 2H), 8.83 (s,1H), 10.6 (s,1H).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated in vacuo
  3. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-2c5fe636f6e4445da72c267f5620b62d
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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