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

HRID 1290067노트

반응식

HRID 1290067 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9327334cfcf54dd5b492bc7a9cdc083a
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750701

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