Ethanesulfonyl chloride → HCID 19348792, compound

HRID 1637444Notes

Reaction equation

HRID 1637444 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH2:18])=[CH:13][C:12]=1[NH:19][C:20](=[O:38])[CH2:21][CH:22]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=1[O:36][CH3:37])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH3:10])([CH3:9])[CH3:8]>C(Cl)Cl.C(OCC)(=O)C>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:13][C:12]=1[NH:19][C:20](=[O:38])[CH2:21][CH:22]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=1[O:36][CH3:37])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 19348478HCID 19348478, compound

Product 1

HCID 19348792HCID 19348792, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

180 μl (1.90 mmol) of ethanesulfonyl chloride and then 213 mg (1.75 mmol) of 4-N,N-dimethylaminopyridine were added to a solution of 700 mg (1.59 mmol) of N-[2-t-butyl-5-(aminomethyl)phenyl]-3-(2,4-dimethoxyphenyl)octanamide (prepared as described in Preparation 26A) in 15 ml of methylene chloride, whilst cooling in an ice-salt bath, and the resulting mixture was stirred at the same temperature for 1 hour. At the end of this time, the reaction mixture was diluted with ethyl acetate, and the diluted solution was washed with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 38 g of silica gel, using a 3:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 360 mg of the title compound as a foam-like substance.

Workup

  1. temperaturewhilst cooling in an ice-salt bath
  2. washthe diluted solution was washed with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialafter which it was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through 38 g of silica gel
  6. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-547f54e9f46c49bea180648f25fb639d
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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