Triethylamine → (1S,4aS,7aR)-7-(chloromethyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester

HRID 1976376ノート

反応式

HRID 1976376 の反応式
[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:18][C@@H:17]3O[C@@:16]3([CH2:20]O)[C@@H:7]2[C@H:8]([O:11][C:12](=[O:15])[NH:13][CH3:14])[O:9][CH:10]=1)=[O:4].C(N(CC)CC)C.CS([Cl:33])(=O)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:18][CH:17]=[C:16]([CH2:20][Cl:33])[C@@H:7]2[C@H:8]([O:11][C:12](=[O:15])[NH:13][CH3:14])[O:9][CH:10]=1)=[O:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86755120(1S,4aS,6S,7R,7aR)-6,7-epoxy-7-(hydroxymethyl)-1-(methylcarbamoyloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta [c] pyrane-4-carboxylic acid methylester

生成物 1

HCID 56979085(1S,4aS,7aR)-7-(chloromethyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester収率 24%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2.0 g of (1S,4aS,6S,7R,7aR)-6,7-epoxy-7 -(hydroxymethyl)-1-(methylcarbamoyloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta [c] pyrane-4-carboxylic acid methylester described in Example 19 were dissolved in dichloromethane followed by addition of 2.5 ml of triethylamine and 1.4 ml of methanesulfonylchloride while stirring and cooling with ice. After stirring for 12 hours at the same temperature, the reaction mixture was extracted with ethyl-acetate. After washing the organic phase with saturated aqueous sodium bicarbonate and brine, it was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a pale yellow oil from the hexane-ether eluate in the form of (1S,4aS,7aR)-7-(chloromethyl)-1-(methylcarbamoyloxy )-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester (770 mg, yield: 24%). The physicochemical properties of this compound are described below.

後処理

  1. temperaturecooling with ice
  2. stirringAfter stirring for 12 hours at the same temperature
  3. extractionthe reaction mixture was extracted with ethyl-acetate
  4. washAfter washing the organic phase with saturated aqueous sodium bicarbonate and brine, it
  5. dry with materialwas dried over magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-44bcc818174d443bbd13476bca6a5152
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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