Carbon Dioxide → HCID 10241131, 화합물

HRID 1989810노트

반응식

HRID 1989810 반응식
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

참가 물질

8

반응물 5

HCID 280Carbon DioxideHCID 24408Bromine2회HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 55302948(3R,5S)-6-Chloro-3,5-dihydroxyhexanal

생성물 1

HCID 10241131HCID 10241131, 화합물수율 82%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-06393535e51b44e5be0e2de653566630
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642363B2

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