Methyl p-toluenesulfonate → HCID 86740533, compound

HRID 637544Notes

Reaction equation

HRID 637544 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]([O:20][C:21](=[O:25])[CH2:22][O:23][CH3:24])[O:17][CH2:18][CH3:19])=[CH:9][CH:8]=1.[C:27]1([CH3:38])[CH:32]=[CH:31][C:30]([S:33]([O:36]C)(=[O:35])=[O:34])=[CH:29][CH:28]=1.[CH:39](OC(C)C)(C)C>C(Cl)Cl>[C:27]1([CH3:38])[CH:28]=[CH:29][C:30]([S:33]([O-:36])(=[O:34])=[O:35])=[CH:31][CH:32]=1.[CH2:18]([O:17][CH:16]([O:20][C:21](=[O:25])[CH2:22][O:23][CH3:24])[CH2:15][CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([NH:6][C:5]([CH2:4][CH2:3][S+:2]([CH3:39])[CH3:1])=[O:26])=[CH:12][CH:11]=1)[CH3:19]

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 7914Diisopropyl EtherHCID 70487297HCID 70487297, compound

Product 1

HCID 86740533HCID 86740533, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolved in 30 ml of methylene chloride was 3.85 g of 2-{4-(3-ethoxy-2-methoxyacetoxypropoxy)phenylcarbamoyl}ethyl methyl sulfide. Thereto was added 5.58 g of methyl p-toluenesulfonate and the mixture was stirred at room temperature for 48 hours. Isopropyl ether was adde to the reaction mixture and the insoluble solid was separated. The solid was purified with acetonitrile-ether, giving 5.30 g of 2-{4-(3-ethoxy-2-methoxyacetoxypropoxy)phenylcarbamoyl}ethyldimethylsulfonium p-toluenesulfonate (Compound 62) in 92.7% yield.

Workup

  1. customthe insoluble solid was separated
  2. customThe solid was purified with acetonitrile-ether

Sources & evidence

ORD record
ord-f8ab5c62293040ab991111c157e3544f
Source dataset
uspto-grants-1985_12
Patent number
US04556737

Reaction notes

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