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

HRID 465560ノート

反応式

HRID 465560 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-18a62a189e304b49b5364dcc056134dd
出典データセット
uspto-grants-1992_10
特許番号
US05153214

反応ノート

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