Potassium Carbonate → 8-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone

HRID 1634727ノート

反応式

HRID 1634727 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:20])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH2:15][CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=C(S(O[CH2:34][C@H:35]2[O:37][CH2:36]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:20][CH2:34][C@@H:35]2[CH2:36][O:37]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH2:15][CH2:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 127517378-(Benzyloxy)-5-hydroxy-3,4-dihydroquinolin-2(1H)-one

生成物 1

HCID 233813448-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone収率 82.1%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

A mixture of 8-(benzyloxy)-5-hydroxy-3,4-dihydro-2(1H)-quinolinone (0.20 g, 0.743 mmol), (S)-(+)-glycidyl 3-nitrobenzenesulfonate (0.193 g, 0.743 mmol) and potassium carbonate (0.113 g, 0.817 mmol) in 2-butanone (10 mL) was heated at reflux for 16 hours. The solvent was removed in vacuo and the residue purified by flash chromatography (chloroform-methanol, 50:1) to yield the title compound (0.210 g, 0.61 mmol).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by flash chromatography (chloroform-methanol, 50:1)

出典と根拠

ORDレコード
ord-60d95559de3842d6aeac341fa2e20646
出典データセット
uspto-grants-2003_01
特許番号
US06506901B2

反応ノート

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