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

HRID 6455

反応式

HRID 6455 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2023d8b66fd14bfc92a109f8fab6f737
出典データセット
uspto-grants-1993_09
特許番号
US05248793

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