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

HRID 1634727노트

반응식

HRID 1634727 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-60d95559de3842d6aeac341fa2e20646
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506901B2

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