Water → (4R-cis)-1,1-dimethylethyl 6-(4-chlorobenzenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetate

HRID 6455

반응식

HRID 6455 반응식
[OH:1][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]1.C(N(CC)CC)C.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.O>C(Cl)Cl>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([O:1][CH2:2][C@H:3]2[O:8][C:7]([CH3:9])([CH3:10])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

생성물 1

HCID 11797121(4R-cis)-1,1-dimethylethyl 6-(4-chlorobenzenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetate수율 130.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirring, 0°-5° C. solution of the (4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (European Patent Application 0319,847) (10 g, 38 mmol) in methylene chloride (250 mL) containing triethylamine (10 mL, 72 mmol) is added 4-chlorobenzenesulfonyl chloride (12.7 g, 60 mmol). Stirring is continued at 0°-5° C. for 2.5 hours and the solution slowly warmed to 20°-25° C. over a period of 2 hours. The solution is poured onto 200 mL of water and the layers separated. The upper aqueous layer is extracted with 200 mL of methylene chloride and the combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution to ensure complete removal of 4-chlorobenzenesulfonyl chloride and then saturated sodium chloride solution. Drying the solution with magnesium sulfate and concentration in vacuo gives 21.5 g of the product as a pale yellow solid.

후처리

  1. temperaturethe solution slowly warmed to 20°-25° C. over a period of 2 hours
  2. customthe layers separated
  3. extractionThe upper aqueous layer is extracted with 200 mL of methylene chloride
  4. washthe combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution
  5. customremoval of 4-chlorobenzenesulfonyl chloride
  6. customDrying the solution
  7. concentrationwith magnesium sulfate and concentration in vacuo

출처 및 근거

ORD 기록
ord-2023d8b66fd14bfc92a109f8fab6f737
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248793

연결된 노트

불러오는 중…