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

HRID 6458

반응식

HRID 6458 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.[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)([O-:28])=[O:27].O>C(Cl)Cl>[N+:26]([C:29]1[CH:30]=[CH:31][C:32]([S:35]([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:37])=[O:36])=[CH:33][CH:34]=1)([O-:28])=[O:27]

참가 물질

6

반응물 4

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

생성물 1

HCID 22847683(4R-cis)-1,1-dimethylethyl 6-(4-nitrobenzenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetate수율 110.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirring 20°-25° 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, 0.038 mol) in methylene chloride (250 mL) containing triethylamine (7 mL, 0.05 mol) is added 4-nitrobenzenesulfonyl chloride (10.5 g, 43 mmol). Stirring is continued at 20°-25° C. for 22 hours, the solution is poured onto 200 mL of water and the layers separated. The upper aqueous layer is extracted with 250 mL of methylene chloride and the combined organic layers are washed with 100 mL each of saturated sodium bicarbonate solution to ensure complete removal of 4-nitrobenzenesulfonyl chloride and then saturated sodium chloride solution. Drying the solution with magnesium sulfate and concentration in vacuo gives 18.7 g of the product as a brown oil which solidifies immediately.

후처리

  1. customthe layers separated
  2. extractionThe upper aqueous layer is extracted with 250 mL of methylene chloride
  3. washthe combined organic layers are washed with 100 mL each of saturated sodium bicarbonate solution
  4. customremoval of 4-nitrobenzenesulfonyl chloride
  5. customDrying the solution
  6. concentrationwith magnesium sulfate and concentration in vacuo

출처 및 근거

ORD 기록
ord-a12e310df1644252937b6e4ef4818172
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248793

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