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 392309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392309
[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

Komponenten

5

Edukt 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

Produkt 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-pyrazinecarboxylateAusbeute 865,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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]

Quellen und Nachweise

ORD-Eintrag
ord-ed4aafc81f2547beaab02ae600a94142
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800629B2

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