Dimethyl Sulfoxide → Methyl 8-(p-chlorophenylsulfonamido)-4-(formylmethyl)octanoate
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([CH2:33][CH2:34][OH:35])[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.CCOCC>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([S:18]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([CH2:33][CH:34]=[O:35])[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])(=[O:19])=[O:20])=[CH:16][CH:17]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
A solution of 0.47 mL dimethylsulfoxide in 19 mL methylene chloride is cooled to -70° C. and 0.41 mL oxalyl chloride is added slowly. The solution is stirred at -70° C. for 15 minutes and a solution of 0.38 g of methyl 8-(p-chlorophenylsulfonamido)-4-(2-hydroxyethyl)octanoate in 1 mL methylene chloride is added slowly. The solution is stirred at -60° C. for 15 minutes and 1.9 mL triethylamine is added. The mixture is allowed to warm up to room temperature, washed with saturated sodium bicarbonate solution, and the organic phase is dried, filtered and evaporated to obtain a yellow oil. This oil is taken up in ether and washed with saturated sodium bicarbonate solution. The ether layer is dried, filtered and evaporated to yield methyl 8-(p-chlorophenylsulfonamido)4-(formylmethyl)-octanoate.
Workup
- stirringThe solution is stirred at -60° C. for 15 minutes
- temperatureto warm up to room temperature
- washwashed with saturated sodium bicarbonate solution
- customthe organic phase is dried
- filtrationfiltered
- customevaporated
- customto obtain a yellow oil
- washwashed with saturated sodium bicarbonate solution
- dry with materialThe ether layer is dried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-957efb7350204eeda3b9a33436f08861
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05025025
Reaction notes
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