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Dichloromethane → HCID 86755119, 화합물

HRID 377084
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HRID 377084 반응식
ClCCl.[CH3:4][O:5][C:6]([C:8]1[C@H:9]2[CH2:17][C@@H:16]3[O:18][C@:15]3([CH3:19])[C@@H:10]2[CH:11]([OH:14])[O:12][CH:13]=1)=[O:7].[Cl:20][CH2:21][C:22]([N:24]=[C:25]=[O:26])=[O:23]>CCCCCC.C(OCC)(=O)C>[CH3:4][O:5][C:6]([C:8]1[C@H:9]2[CH2:17][C@@H:16]3[O:18][C@:15]3([CH3:19])[C@@H:10]2[C@@H:11]([O:14][C:25](=[O:26])[NH:24][C:22](=[O:23])[CH2:21][Cl:20])[O:12][CH:13]=1)=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 78209Chloroacetyl isocyanateHCID 57213576HCID 57213576, 화합물

생성물 1

HCID 86755119HCID 86755119, 화합물수율 91%

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

실험 절차

A dichloromethane solution containing 100 mg of a known (4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-hydroxy-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester was cooled with ice followed by addition of chloroacetylisocyanate (45 ml) and stirring for 15 hours at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless powder from the hexane-ethyl acetate eluate in the form of (1R,4aS,6S,7R,7aR)-1-(chloroacetylcarbamoyloxy)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester (137 mg, yield: 91%). The physicochemical properties of this compound are described in Table 8, Compound No. 40.

후처리

  1. temperaturewas cooled with ice
  2. extractionThe reaction mixture was then extracted with dichloromethane
  3. washAfter washing the organic phase with brine, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-24445cea31a04fff84da3732fafa7c35
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06022888

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