Carbon Dioxide → 2,2'-Anhydro-1-beta-arabinofuranosylthymine

HRID 1379291

Reaktionsgleichung

Reaktionsgleichung von HRID 1379291
[CH3:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1O.C(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C(=O)=O.CCOC(C)=O>CN(C)P(N(C)C)(N(C)C)=O.C(=O)(O)[O-].[Na+]>[CH3:1][C:2]1[C:3](=[O:18])[N:4]=[C:5]2[N:6]([C@@H:7]3[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@@H:8]3[O:17]2)[CH:16]=1

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 7597Diphenyl carbonateHCID 8857Ethyl AcetateHCID 4454085-Methyluridine

Produkt 1

HCID 1680452,2'-Anhydro-1-beta-arabinofuranosylthymineAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 516892Sodium BicarbonateKatalysatorHCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 5-methyluridine (16.77 g, 69.2 mmol), diphenyl carbonate (17.8 g, 83.1 mmol) and sodium bicarbonate (100 mg) in hexamethylphosphoramide (175 ml) was heated to 150° C. with stirring until evolution of CO2 ceased (approximately 1 hr). The reaction mixture was cooled and then poured into diethylether (11) while stirring to furnish a brown gum. Repeated washings with diethylether (4×250 ml) furnished a straw colored hygroscopic powder. The solid was purified by short column chromatography on silica gel (400 g). Pooling and concentration of appropriate fractions, which were eluted with CH2Cl2 -MeOH (85:15, v/v) furnished the title compound as a straw colored solid (12 g, 77.3%) which crystallized from EtOH as long needles, m.p. 226°-227° C.

Aufarbeitung

  1. custom(approximately 1 hr)
  2. temperatureThe reaction mixture was cooled
  3. customto furnish a brown gum
  4. washRepeated washings with diethylether (4×250 ml)
  5. customfurnished a straw colored hygroscopic powder
  6. customThe solid was purified by short column chromatography on silica gel (400 g)
  7. washPooling and concentration of appropriate fractions, which were eluted with CH2Cl2 -MeOH (85:15, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-18b3d4c79ba0411b82071a33d59199b4
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05670633

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