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

HRID 6458
Notes
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Reaction equation

HRID 6458 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.[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

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, 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.

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 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

Sources & evidence

ORD record
ord-a12e310df1644252937b6e4ef4818172
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05248793

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes