Triethylamine → Methyl 8-(p-chlorophenylsulfonamido)-4-(2-methylsulfonyloxyethyl)-octanoate

HRID 465555Notes

Reaction equation

HRID 465555 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][OH:25])[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][O:25][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10069054Methyl 8-(p-chlorophenylsulfonamido)-4-(2-hydroxyethyl)octanoate

Product 1

HCID 10050375Methyl 8-(p-chlorophenylsulfonamido)-4-(2-methylsulfonyloxyethyl)-octanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.174 g of methyl 8-(p-chlorophenylsulfonamido)-4-(2-hydroxyethyl)octanoate in 2 ml methylene chloride is cooled to 0° and 0.1 ml of triethylamine is added followed by 0.042 ml of methylsulfonyl chloride. After 1 h, the reaction mixture is washed with saturated sodium bicarbonate and the organic layer is dried, filtered and evaporated to yield methyl 8-(p-chlorophenylsulfonamido)-4-(2-methylsulfonyloxyethyl)-octanoate as an oil.

Workup

  1. washthe reaction mixture is washed with saturated sodium bicarbonate
  2. customthe organic layer is dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-b2f4c6e01f1d4d56b03f96c3c1f2e350
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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