HCID 23592307, compound → HCID 23592308, compound

HRID 1611671Notes

Reaction equation

HRID 1611671 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[Cl:26])[C@H:12]([CH3:18])[CH:13]([OH:17])[CH2:14][CH:15]=[CH2:16])(=[O:10])=[O:9])=[CH:4][CH:3]=1>CCO.[Pt]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[Cl:26])[C@H:12]([CH3:18])[CH:13]([OH:17])[CH2:14][CH2:15][CH3:16])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 23592307HCID 23592307, compound

Product 1

HCID 23592308HCID 23592308, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-chloro-N-(2,5-dichlorophenyl)-N-(1R)(2-hydroxy-1-methylpent-4-enyl)benzenesulfonamide (150 mg, 0.3 mmol) and sulfided platinum (5 wt. % on carbon, 50 mg) in EtOH (50 mL) was hydrogenated at 45 psi for 3 h. The suspension was filtered through celite and concentrated in vacuo. Silica gel chromatography (10% EtOAc/hexanes) of the concentrate afforded the title compound as a clear wax (120 mg, 80% yield): MS (ESI): (M−H)−436.34; [α]D=−15.3° (c 1.00, MeOH), 1H NMR (DMSO-d6) δ 7.81 (d, 2H, J=7.0 Hz), 7.60 (d, 2H,) J=7.0 Hz), 7.50 (s, br, 1H), 7.41 (d, 2H, J=8.0 Hz), 7.32 (m, 2H), 7.24 (m, 1H), 7.18 (s, br, 1H), 4.76 (dd, 2H, J=50 Hz, 15 Hz), 4.36 (t, 1H, J=7.0 Hz), 3.33 (s, 3H), 1.20–1.34 (m, 3H), 0.79 (d, 3H, J=6.0 Hz), 0.46 (d, 3H, J=6.0 Hz).

Workup

  1. filtrationThe suspension was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-389737f7aaf24d319e48c9be4560bea0
Source dataset
uspto-grants-2006_01
Patent number
US06989399B2

Reaction notes

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