Dichloromethane → (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid 4-methylpiperazylamide

HRID 377079

반응식

HRID 377079 반응식
ClCCl.[O:4]1[C@@:21]2([CH3:22])[C@@H:5]1[CH2:6][C@@H:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][O:10][C@@H:9]([O:16][C:17](=[O:20])[NH:18][CH3:19])[C@H:8]12.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.[Cl-].ClC1N(C)CC[NH+:33]1C>ClCCl.CO.C(N(CC)CC)C>[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([NH:33][C:13]([C:12]2[C@H:7]3[CH2:6][C@@H:5]4[O:4][C@:21]4([CH3:22])[C@@H:8]3[C@H:9]([O:16][C:17](=[O:20])[NH:18][CH3:19])[O:10][CH:11]=2)=[O:15])[CH2:26][CH2:25]1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 531671-MethylpiperazineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 18397301(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid

생성물 1

HCID 86755118(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid 4-methylpiperazylamide수율 50%

시약·촉매·용매 2

HCID 8471Triethylamine용매HCID 21226129Dichloromethane methanol용매

실험 절차

A dichloromethane solution containing 400 mg of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid described in Example 1 was cooled with ice followed by addition of 0.20 ml of 1-methylpiperazine, 2 ml of triethylamine and 301 mg of 2-chloro-1,3-dimethylimidazolinium chloride and stirring for 15 hours at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with saturated aqueous sodium bicarbonate and 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 dichloromethane-methanol eluate in the form of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid 4-methylpiperazylamide (264 mg, yield: 50%). The physicochemical properties of this compound are described in Table 5, Compound No. 20.

후처리

  1. temperaturewas cooled with ice
  2. extractionThe reaction mixture was then extracted with dichloromethane
  3. washAfter washing the organic phase with saturated aqueous sodium bicarbonate and 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-64f12ff0751e459ba46fcba4a05619e9
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022888

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