2′,3′,5′-Tri-O-acetyluridine → Uridine

HRID 2184094Notes

Reaction equation

C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:26]=[CH:25][C:23](=[O:24])[NH:22][C:20]1=[O:21])(=O)C>CO.N>[C@@H:6]1([N:19]2[CH:26]=[CH:25][C:23](=[O:24])[NH:22][C:20]2=[O:21])[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

Conditions

Temperature: 23 °C

Procedure

1.2 g (purity 80%) of uridine triacetate obtained in EXAMPLE 1 was dissolved in 9.4 ml of a 2 M ammonia methanol solution and stirred at room temperature (23° C.). After the completion of the reaction, the solvent was distilled off to give 0.7 g of crude uridine (purity 87%) as a white solid. Ethanol in an amount 48.5 times by volume as much as the crude uridine was added and uridine was completely dissolved herein by heating to 58° C. Next, the solution was allowed to cool to room temperature (23° C.) and aged for 30 minutes. Then, it was cooled to 5° C. and aged for 30 minutes. The precipitated white crystals were filtered, washed and dried to give 0.3 g of β-uridine (purity 97%). 1H-NMR (400 MHz, in D2O): δ=3.76 (dd, J=12.6, 4.3 Hz, 1H), 3.87 (dd, J=12.6, 2.8 Hz, 1H), 4.09 (m, 1H), 4.18 (m, 1H), 4.31 (m, 1H), 5.86 (m, 1H), 7.83 (d, J=8.1 Hz, 1H)

Workup

customAfter the completion of the reaction
distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-b7f6ad688ac247a4b06f29d14c8ec733
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900298B2

Reaction notes

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