Potassium Carbonate → 5-(2R)-2-Oxiranyl-8-(phenylmethoxy)-2(1H)-quinolinone

HRID 1290067ノート

反応式

HRID 1290067 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:23])[CH2:21]Cl)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]2[CH2:21][O:23]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 118096612(1H)-Quinolinone, 5-[(1R)-2-chloro-1-hydroxyethyl]-8-(phenylmethoxy)-

生成物 1

HCID 114378125-(2R)-2-Oxiranyl-8-(phenylmethoxy)-2(1H)-quinolinone

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
60 °C

実験手順

A suspension of (R)-8-benzyloxy-5-(2-chloro-1-hydroxyethyl)carbostyril (130 mg, 0.4 mMol) in acetone (10 ml) containing potassium carbonate (276 mg, 2 mMol) was stirred at 60° C. under an argon atmosphere for 18 hours. After cooling, the suspension was filtered and the filter pad was washed with acetone. The filtrates were combined and evaporated. Purification of the residue by chromatography on silica gel eluting with ethyl acetate gave the title compound as a pale yellow solid; m.p. 146°-150° C.; [α]D25 -30° (c=0.91, chloroform).

後処理

  1. temperatureAfter cooling
  2. filtrationthe suspension was filtered
  3. washthe filter pad was washed with acetone
  4. customevaporated
  5. customPurification of the residue by chromatography on silica gel eluting with ethyl acetate

出典と根拠

ORDレコード
ord-9327334cfcf54dd5b492bc7a9cdc083a
出典データセット
uspto-grants-1998_05
特許番号
US05750701

反応ノート

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