[(2S,3S,4S,5S)-3,4-dibenzoyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate → 1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidine-2,4-dione

HRID 744163Notes

Reaction equation

HRID 744163 reaction equation
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[CH:41]=[C:40]([F:42])[C:38](=[O:39])[NH:37][C:35]1=[O:36])(=O)C1C=CC=CC=1>N.CO>[C@H:11]1([N:34]2[CH:41]=[C:40]([F:42])[C:38](=[O:39])[NH:37][C:35]2=[O:36])[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

3

Reactant 1

HCID 13827065[(2S,3S,4S,5S)-3,4-dibenzoyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate

Product 1

HCID 52705261-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidine-2,4-dioneYield 96.8%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

Compound 5 (0.75 g, 1.30 mmol) in NH3 /MeOH (100 ml) was stirred at room temperature overnight and worked up as in Example 1, Step C to give pure 6 (0.33 g, 96%) as white crystals: m.p. 147°-148° C.

Sources & evidence

ORD record
ord-bb5f3bc728284f208363b3a00dfa973a
Source dataset
uspto-grants-1996_09
Patent number
US05559101

Reaction notes

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