Triethylamine → (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 geranyl ester

HRID 377075노트

반응식

HRID 377075 반응식
C(N(CC)CC)C.C(OP(Cl)(OCC)=O)C.[O:17]1[C@@:34]2([CH3:35])[C@@H:18]1[CH2:19][C@@H:20]1[C:25]([C:26]([OH:28])=[O:27])=[CH:24][O:23][C@@H:22]([O:29][C:30](=[O:33])[NH:31][CH3:32])[C@H:21]12.[CH3:36][C:37](=[CH:39][CH2:40][CH2:41]/[C:42](=[CH:44]/[CH2:45]O)/[CH3:43])[CH3:38]>CN(C)C1C=CN=CC=1.CCCCCC.C(OCC)(=O)C.ClCCl>[CH2:45]([O:27][C:26]([C:25]1[C@H:20]2[CH2:19][C@@H:18]3[O:17][C@:34]3([CH3:35])[C@@H:21]2[C@H:22]([O:29][C:30](=[O:33])[NH:31][CH3:32])[O:23][CH:24]=1)=[O:28])/[CH:44]=[C:42](/[CH2:41][CH2:40][CH:39]=[C:37]([CH3:38])[CH3:36])\[CH3:43]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 637566GeraniolHCID 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 86755114(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 geranyl ester수율 50%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 21226206Ethyl acetate hexane용매

실험 절차

0.5 ml of triethylamine and 0.45 ml of diethylchlorophosphate were added to a dichloromethane solution containing 331 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. After stirring for 30 minutes at room temperature, 0.42 ml of geraniol and 17 mg of 4-dimethylaminopyridine (to be abbreviated as DMAP) were added followed by stirring for 5 hours at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with dilute hydrochloric acid, 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 oil from the hexane-ethyl acetate 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 geranyl ester (280 mg, yield: 50%). The physicochemical properties of this compound are described in Table 2, Compound No. 6.

후처리

  1. stirringby stirring for 5 hours at room temperature
  2. extractionThe reaction mixture was then extracted with dichloromethane
  3. washAfter washing the organic phase with dilute hydrochloric acid, 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-fb824a0c022041db86ae7416c315e961
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022888

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