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Dimethyl Sulfoxide → (3R,4S,5R)-3-Azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

HRID 492255
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HRID 492255 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[C@H:9]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[C@H:8](OS(C)(=O)=O)[CH:7]=1)=[O:5])[CH3:2].CS(C)=O.[N-:31]=[N+:32]=[N-:33].[Na+]>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[C@@H:9]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[C@H:8]([N:31]=[N+:32]=[N-:33])[CH:7]=1)=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium Azide2회HCID 42643351(3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

생성물 1

HCID 86628951(3R,4S,5R)-3-Azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester수율 70.5%

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

실험 절차

A 5 mL round-bottom flask equipped with a magnetic stirrer and an inert gas supply was charged with 436.3 mg of 12 and 0.83 mL DMSO. To the clear colorless solution at RT was added 71.5 mg sodium azide and the reaction mixture was stirred for 2.5 h, then an additional 13.7 mg of sodium azide were added and stirring continued at RT for 19 h. The reaction mixture was diluted with 5 mL of EtOAc and extracted three times with a 1 M solution of NaHCO3. The organic phase was separated, dried (Na2SO4), filtered and evaporated at 20° C./140-10 mbar to obtain 0.33 g of the crude product as light yellow oil. The crude product was purified by SiO2 column chromatography eluting with a ½ mixture of EtOAc and n-hexane. The combined fractions were evaporated and dried on a rotary evaporator to obtain 0.27 g of 14 as a colorless oil

후처리

  1. customA 5 mL round-bottom flask equipped with a magnetic stirrer
  2. stirringstirring
  3. waitcontinued at RT for 19 h
  4. extractionextracted three times with a 1 M solution of NaHCO3
  5. customThe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated at 20° C./140-10 mbar
  9. customto obtain 0.33 g of the crude product as light yellow oil
  10. customThe crude product was purified by SiO2 column chromatography
  11. washeluting with a ½ mixture of EtOAc and n-hexane
  12. customThe combined fractions were evaporated
  13. customdried on a rotary evaporator

출처 및 근거

ORD 기록
ord-e3e4b0a6579f43dc8853fe5088c4e146
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07531687B2

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