HCID 23592304, compound → HCID 23592309, compound

HRID 1611669Notes

Reaction equation

HRID 1611669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:37]2[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=2[Cl:44])[C@H:12]([CH3:36])[CH2:13][CH2:14][CH2:15][O:16]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:37]2[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=2[Cl:44])[C@H:12]([CH3:36])[CH2:13][CH2:14][CH2:15][OH:16])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 23592304HCID 23592304, compound

Product 1

HCID 23592309HCID 23592309, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-N-(2,5-dichlorophenyl)-N-(1R)(1-methyl-4-trityloxybutyl)benzenesulfonamide (5.25 g, 8.0 mmol) was treated with amberlyst 15 (excess, 50 g) in MeOH (150 mL) at room temperature. After 18 h the amberlyst was removed by filtration and the filtrate was concentrated in vacuo. Silica gel chromatography (20% EtOAc/hexanes) of the concentrate afforded 4-chloro-N-(2,5-dichlorophenyl)-N-(1R)(4-hydroxy-1-methylbutyl)benzenesulfonamide (3.75 g, 63% yield): 1H NMR (CDCl3) δ 7.74 (d, 2H, J=8.2 Hz), 7.34–7.52 (m, 5H), 4.18–4.41 (m, 1H), 3.35–3.61 (m, 2H), 1.61–1.72 (m, 2H), 1.77 (s, br, 1H), 1.05–1.09 (m, 3H)

Workup

  1. customAfter 18 h the amberlyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f941102a59d7441680e6c31a26db2204
Source dataset
uspto-grants-2006_01
Patent number
US06989399B2

Reaction notes

Loading…