Trimethyl orthoformate → methyl 4-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate

HRID 392309노트

반응식

HRID 392309 반응식
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[C:11]1=[O:20].C(OC)(OC)OC.O.[C:29]1(C)[CH:34]=CC(S(O)(=O)=O)=C[CH:30]=1>CC(C)=O>[OH:9][CH2:8][C@@H:5]1[C@H:6]2[O:7][C:29]([CH3:34])([CH3:30])[O:1][C@H:2]2[C@H:3]([N:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[C:11]2=[O:20])[O:4]1

참가 물질

5

반응물 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 11492964methyl 4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate

생성물 1

HCID 60126642methyl 4-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate수율 865.6%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

In 5 mL of acetone was suspended 0.50 g of methyl 4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate. Then, 1 ml of trimethyl orthoformate and 33 mg of p-toluenesulfonic acid monohydrate were successively added, the mixture thus obtained was heated under reflux for one hour, and the solvent was removed under reduced pressure. By purifying the residue by column chromatography [eluent: ethyl acetate], 0.49 g of methyl 4-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate was obtained as a white-colored solid product.

후처리

  1. customthe mixture thus obtained
  2. temperaturewas heated
  3. temperatureunder reflux for one hour
  4. customthe solvent was removed under reduced pressure
  5. customBy purifying the residue by column chromatography [eluent: ethyl acetate]

출처 및 근거

ORD 기록
ord-ed4aafc81f2547beaab02ae600a94142
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800629B2

반응 노트

불러오는 중…