p-Toluenesulfonic acid → Diethyl 2-ethyloxazolo[5,4-b]pyridine-5,6-dicarboxylate

HRID 864910

반응식

HRID 864910 반응식
[NH2:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:3]=1.C(O[C:22](OCC)(OCC)[CH2:23][CH3:24])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:23]([C:24]1[O:8][C:7]2[C:2]([N:1]=1)=[CH:3][C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]=2)[CH3:22]

참가 물질

4

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 66995Ethyl orthopropionateHCID 19958246Diethyl 5-amino-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

생성물 1

HCID 19958240Diethyl 2-ethyloxazolo[5,4-b]pyridine-5,6-dicarboxylate수율 84.8%

실험 절차

Diethyl 5-amino-1,6-dihydro-6-oxo-pyridine-2,3-dicarboxylate (7.57 g, 0.030 mol), is suspended in 60 mL triethylorthopropionate (TEOP 0.30 mol). A small amount of p-toluenesulfonic acid is added and the mixture is heated at reflux for 65 hours. The triethylorthopropionate is removed in vacuo and the resulting oil is purified by column chromatography. The tractions containing the pure desired product are combined and stripped to a honey-colored oil weighing 7.38 g, yield 84.8%.

후처리

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 65 hours
  3. customThe triethylorthopropionate is removed in vacuo
  4. customthe resulting oil is purified by column chromatography
  5. additionThe tractions containing the pure desired product

출처 및 근거

ORD 기록
ord-49c9fb86762a46aaacbfc45b2f05c092
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565411

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