Methanol → HCID 68978433, compound

HRID 1516276Notes

Reaction equation

HRID 1516276 reaction equation
C([O:9][CH2:10][C@@H:11]1[C:15]([O:17]C(=O)C)([CH3:16])[C@:14]([F:22])([CH3:21])[CH:13]([N:23]2[CH:28]=[CH:27][C:26](=[O:29])[NH:25][C:24]2=[O:30])[O:12]1)(=O)C1C=CC=CC=1.CO>N>[F:22][C:14]1([CH3:21])[C@@:15]([OH:17])([CH3:16])[CH:11]([CH2:10][OH:9])[O:12][C@H:13]1[N:23]1[CH:28]=[CH:27][C:26](=[O:29])[NH:25][C:24]1=[O:30]

Participants

4

Reactant 2

HCID 887MethanolHCID 57867363HCID 57867363, compound

Product 1

HCID 68978433HCID 68978433, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of ((2R,4R)-3-acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 0.25 g, 0.59 mmol) in methanolic ammonia (25% w/w 10 ml) was stirred at room temperature for overnight. Completion of the reaction mixture monitored by thin-layer chromatography and methanol was removed under reduced pressure. Water added to the crude and extracted with ethyl acetate and the organic layer was dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 5% methanol in dichloromethane to elude title compound (0.09 g). Yield: 55%; 1H-NMR: 1H NMR (300 MHz, CDCl3): δ 8.57 (bs, 1H), 7.38-7.33 (m, 1H), 6.44 (d, 1H, J=22.2 Hz), 5.73 (d, 1H, J=8.1 Hz), 4.65 (bs, 1H), 4.19-4.09 (m, 3H), 2.86 (bs, 1H), 1.48 (s, 3H), 1.35 (d, 3H, J=2.6 Hz); ES Mass: [M+Na]+: 297 (20%), [M+1]+ 275 (20%); IR cm−: 3430 2928, 2864, 2273, 1707, 1385, 1270, 1052, 821, 567; HPLC: 93.2%.

Workup

  1. customwas removed under reduced pressure
  2. additionWater added to the crude
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic layer was dried over sodium sulphate
  5. concentrationConcentration
  6. customunder reduced pressure and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-913575a39071489e81379eaff8c125d7
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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