Methyl p-toluenesulfonate → HCID 86740535, compound

HRID 637545Notes

Reaction equation

HRID 637545 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([S:7]([O:10]C)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:13][S:14][CH2:15][CH2:16][C:17](=[O:43])[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][CH:28]([O:36][C:37](=[O:42])[CH2:38][C:39](=[O:41])[CH3:40])[O:29][C:30](=[O:35])[NH:31][CH2:32][CH2:33][CH3:34])[CH:20]=1>CCOCC>[C:1]1([CH3:12])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[C:39]([CH2:38][C:37]([O:36][CH:28]([O:29][C:30](=[O:35])[NH:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:26][O:25][C:21]1[CH:20]=[C:19]([NH:18][C:17]([CH2:16][CH2:15][S+:14]([CH3:1])[CH3:13])=[O:43])[CH:24]=[CH:23][CH:22]=1)=[O:42])(=[O:41])[CH3:40]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 70487589HCID 70487589, compound

Product 1

HCID 86740535HCID 86740535, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 5.5 g quantity of methyl p-toluenesulfonate was added to 4.54 g of 2-{3-(2-acetylacetyloxy-3-propylcarbamoyloxypropoxy)phenylcarbamoyl}ethyl methyl sulfide. The mixture was stirred at room temperature for 24 hours. Ether was added to the reaction mixture. The insoluble solid was filtered off, and was recrystallized from acetonitrile-ether, giving 6.10 g of 2-{3-(2-acetylacetyloxy-3-propylcarbamoyloxypropoxy)phenylcarbamoyl}ethyldimethylsulfonium p-toluenesulfonate in 95.2% yield, M.P. 74° to 76° C.

Workup

  1. filtrationThe insoluble solid was filtered off
  2. customwas recrystallized from acetonitrile-ether

Sources & evidence

ORD record
ord-521b84a6a1fd4136948132210f3d3973
Source dataset
uspto-grants-1985_12
Patent number
US04556737

Reaction notes

Loading…