Carbon Dioxide → HCID 10241131, compound

HRID 1669906Notes

Reaction equation

HRID 1669906 reaction equation
BrBr.[Cl:3][CH2:4][C@@H:5]([OH:12])[CH2:6][C@@H:7]([OH:11])[CH2:8][CH:9]=[O:10].C(=O)(O)[O-].[Na+].C(=O)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.O>[OH:11][C@@H:7]1[CH2:6][C@@H:5]([CH2:4][Cl:3])[O:12][C:9](=[O:10])[CH2:8]1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 24408Bromine2×HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 55302948(3R,5S)-6-Chloro-3,5-dihydroxyhexanal

Product 1

HCID 10241131HCID 10241131, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

At room temperature 2.1 ml bromine was added in 45 minutes to a mixture of 6.7 g (40 mmol) 6-chloro-2,4,6-trideoxy-D-erythro-hexose (compound I; prepared according to the method described in WO-A-96/31615) and 6.7 g sodium bicarbonate in 40 ml methylene chloride and 10 ml water. CO2 gas escaped, while the pH remained at 5. After stirring for one hour, according to gas-liquid chromatography (GLC) the starting material had been fully converted. The bromine excess was neutralized with solid Na2S2O3. After phase separation the water phase was extracted with 2 times 100 ml ethyl acetate. The combined organic phases were dried over Na2SO4 and filtered. After rotavap evaporation 5.5 g yellow oil was obtained (82% yield of the compound of formula (2) with X=Cl relative to compound I).

Workup

  1. customprepared
  2. customAfter phase separation the water phase
  3. extractionwas extracted with 2 times 100 ml ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customAfter rotavap evaporation 5.5 g yellow oil

Sources & evidence

ORD record
ord-1b648f8cbbad4b7fb703f71f109228c9
Source dataset
uspto-grants-2011_08
Patent number
US07989643B2

Reaction notes

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