Potassium Bromide → tert-Butyl 3,5-dideoxy-2,4-O-(1-methylethylidene)-L-erythro-hexuronate

HRID 877954Notes

Reaction equation

HRID 877954 reaction equation
C1C2CC3N([O])C(C2)CC1C3.[Br-].[K+].[OH:14][CH2:15][C@H:16]1[O:21][C:20]([CH3:23])([CH3:22])[O:19][C@@H:18]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:17]1.Cl[O-].[Na+]>C(Cl)Cl>[CH:15]([C@H:16]1[O:21][C:20]([CH3:23])([CH3:22])[O:19][C@@H:18]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:17]1)=[O:14]

Participants

6

Reactant 4

HCID 253877Potassium BromideHCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonateHCID 23665760Sodium HypochloriteHCID 42643072(2-Azatricyclo[3.3.1.1~3,7~]decan-2-yl)oxidanyl

Product 1

HCID 9881588tert-Butyl 3,5-dideoxy-2,4-O-(1-methylethylidene)-L-erythro-hexuronate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the −15° C. to −5° C. pre-cooled reaction mixture of AZADO (0.002 g), potassium bromide (0.22 g) and methylene chloride (30 ml) added 5 g of tert-butyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate. Stirred the reaction mixture for 15 minutes at −15° C. to −5° C. 19 ml of sodium hypochlorite solution was added to the reaction mixture at same temperature. Stirred the reaction mixture for 15 minutes. Quenched the reaction mixture with 10% aqueous sodium thiosulfate solution. 20 ml of water was added and separated the both aqueous and organic layers. Washed the organic layer with water followed by brine solution. Distilled off the solvent completely to get the title compound as a solid.

Workup

  1. temperatureTo the −15° C. to −5° C. pre-cooled
  2. stirringStirred the reaction mixture for 15 minutes
  3. customQuenched the reaction mixture with 10% aqueous sodium thiosulfate solution
  4. addition20 ml of water was added
  5. customseparated the both aqueous and organic layers
  6. washWashed the organic layer with water
  7. distillationDistilled off the solvent completely

Sources & evidence

ORD record
ord-38cfc2d0ed21467189403a902cbdd5ae
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

Loading…