Ethanethiol → N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-2-ethylsulfanyl-ethanesulfonamide

HRID 2354261Notes

Reaction equation

HRID 2354261 reaction equation
[CH2:1]([SH:3])[CH3:2].[H-].[Na+].[CH3:6][C:7]([CH3:39])([CH3:38])[C:8](=[O:37])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:22]2[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH2:32][CH2:33]Cl)(=[O:31])=[O:30])=[C:24]([CH3:35])[CH:23]=2)([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][C:12]=1[CH3:36]>C1COCC1>[CH3:6][C:7]([CH3:39])([CH3:38])[C:8](=[O:37])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:22]2[CH:27]=[CH:26][C:25]([NH:28][S:29]([CH2:32][CH2:33][S:3][CH2:1][CH3:2])(=[O:31])=[O:30])=[C:24]([CH3:35])[CH:23]=2)([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][C:12]=1[CH3:36]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 58775973N-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-2-chloro-ethanesulfonamide

Product 1

HCID 11353120N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-2-ethylsulfanyl-ethanesulfonamideYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 0° C. solution of ethanethiol (0.1 mL, 1.35 mmol) in THF (5 mL) is treated with NaH (81 mg, 2 mmol, 60% in mineral oil) and stirred for 10 m. The mixture is added a solution of N-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-2-chloro-ethanesulfonamide (500 mg, 1 mmol) in THF (10 mL), warmed to RT, and stirred overnight. The reaction is concentrated, dissolved in CH2Cl2, and washed with 0.2 N HCl. The organic layer is concentrated and chromatographed (0%-20% EtOA/Hex) to give the title compound (270 mg, 51%).

Workup

  1. stirringstirred overnight
  2. concentrationThe reaction is concentrated
  3. dissolutiondissolved in CH2Cl2
  4. washwashed with 0.2 N HCl
  5. concentrationThe organic layer is concentrated
  6. customchromatographed (0%-20% EtOA/Hex)

Sources & evidence

ORD record
ord-482aa6dff117458fb2fce94636dcc17a
Source dataset
uspto-grants-2010_07
Patent number
US07750184B2

Reaction notes

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