Diethyl Sulfate → (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 ethylester

HRID 1976357ノート

反応式

HRID 1976357 の反応式
C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:11][CH3:12])(=O)=O.C(#N)C.[O:19]1[C@@:36]2([CH3:37])[C@@H:20]1[CH2:21][C@@H:22]1[C:27]([C:28]([OH:30])=[O:29])=[CH:26][O:25][C@@H:24]([O:31][C:32](=[O:35])[NH:33][CH3:34])[C@H:23]12>CCCCCC.C(OCC)(=O)C>[CH2:11]([O:29][C:28]([C:27]1[C@H:22]2[CH2:21][C@@H:20]3[O:19][C@:36]3([CH3:37])[C@@H:23]2[C@H:24]([O:31][C:32](=[O:35])[NH:33][CH3:34])[O:25][CH:26]=1)=[O:30])[CH3:12]

参加物

6

反応物 4

HCID 6163Diethyl SulfateHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 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

生成物 1

HCID 57256006(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 ethylester収率 88%

試薬・触媒・溶媒 1

HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
70 °C

実験手順

130 mg of potassium carbonate and 121 μl of diethyl sulfate were added to an acetonitrile solution containing 210 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 followed by heating and stirring for 1 hour at 70° C. The reaction mixture was then extracted with ethyl acetate. 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 ethylester (204 mg, yield: 88%). The physicochemical properties of this compound are described in Table 1, Compound No. 4.

後処理

  1. temperatureby heating
  2. extractionThe reaction mixture was then extracted with ethyl acetate
  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

出典と根拠

ORDレコード
ord-e7ef0ea2a7be467b9c1e6260a4a8abdb
出典データセット
uspto-grants-2001_05
特許番号
US06225478B1

反応ノート

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