p-Toluenesulfonic acid monohydrate → 4-Toluenesulfonic acid 3-(4-chlorobenzyl)-1-methyl-2-oxo-cyclopentylmethyl ester

HRID 922738ノート

反応式

HRID 922738 の反応式
COC([C:5]1([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:9][CH2:8][C:7]([CH2:11][O:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])([CH3:10])[C:6]1=[O:23])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][CH:5]2[CH2:9][CH2:8][C:7]([CH2:11][O:12][S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:14])=[O:15])([CH3:10])[C:6]2=[O:23])=[CH:30][CH:29]=1

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 867182551-(4-Chlorobenzyl)-3-(4-toluenesulfonyloxy)methyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

生成物 1

HCID 867182584-Toluenesulfonic acid 3-(4-chlorobenzyl)-1-methyl-2-oxo-cyclopentylmethyl ester収率 79.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

To 521 mg of Compound 3-1-2 synthesized in Production Example 3, 256 mg of 4-toluenesulfonic acid monohydrate and 32.3 μl of water were added, and the resulting mixture was stirred at 80° C. for 38.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethyl acetate was then carried out. The extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled away. The residue was purified by silica gel column chromatography to obtain 361.1 mg of Compound 4-1-2.

後処理

  1. additionwere added
  2. additionwas added to the reaction solution
  3. customthus obtained
  4. extractionextraction with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine
  6. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-f48158fd031847b497774f4f33eb83cc
出典データセット
uspto-grants-2016_03
特許番号
US09278966B2

反応ノート

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