Dimethyl Sulfoxide → Methyl 8-(p-chlorophenylsulfonamido)-4-(formylmethyl)octanoate

HRID 465560Notes

Reaction equation

HRID 465560 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][O:35]S(C)(=O)=O)[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]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10050375Methyl 8-(p-chlorophenylsulfonamido)-4-(2-methylsulfonyloxyethyl)-octanoate

Product 1

HCID 10340312Methyl 8-(p-chlorophenylsulfonamido)-4-(formylmethyl)octanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.47 ml dimethylsulfoxide in 19 ml methylene chloride is cooled to -70° and 0.41 ml oxalyl chloride is added slowly. The solution is stirred at -70° for 15 min and a solution of 0.38 g of methyl 8-(p-chlorophenylsulfonamido)-4-(2-hydroxyethyl)-octanoate (example 28) in 1 ml methylene chloride is added slowly. The solution is stirred at -60° for 15 min 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

  1. stirringThe solution is stirred at -60° for 15 min
  2. washwashed with saturated sodium bicarbonate solution
  3. customthe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customto obtain a yellow oil
  7. washwashed with saturated sodium bicarbonate solution
  8. dry with materialThe ether layer is dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-18a62a189e304b49b5364dcc056134dd
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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