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

HRID 1494104노트

반응식

HRID 1494104 반응식
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]=1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10069054Methyl 8-(p-chlorophenylsulfonamido)-4-(2-hydroxyethyl)octanoate

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

반응 조건

온도
-70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-957efb7350204eeda3b9a33436f08861
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05025025

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