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

HRID 6454

Reaction equation

HRID 6454 reaction equation
[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.[Br: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>[Br: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

Participants

6

Reactant 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

Product 1

HCID 10917799(4R cis)-1,1,-dimethylethyl 6-(4-bromobenzenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetateYield 144.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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, 38 mmol) in methylene chloride) (250 mL) containing triethylamine (10 mL, 72 mmol) is added 4-bromobenzenesulfonyl chloride (15 g, 57.5 mmol). Stirring is continued at 20°-25° C. for 20 hours, the solution is poured onto 250 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 200 mL each of saturated sodium bicarbonate solution, to ensure complete removal of 4-bromobenzenesulfonyl chloride and then saturates sodium chloride solution. Drying the solution with magnesium sulfate and concentration in vacuo gives 26.3 g of the product as a light orange solid.

Workup

  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 200 mL each of saturated sodium bicarbonate solution
  4. customremoval of 4-bromobenzenesulfonyl chloride
  5. customDrying the solution
  6. concentrationwith magnesium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-acde304896214d548673d4710d7c0098
Source dataset
uspto-grants-1993_09
Patent number
US05248793

Linked notes

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