Water → HCID 57867377, compound

HRID 1516284Notes

Reaction equation

HRID 1516284 reaction equation
[F:1][C:2]1([CH3:19])[C@@:6]([OH:8])([CH3:7])[CH:5]([CH2:9][OH:10])[O:4][C@H:3]1[N:11]1[CH:16]=[CH:15][C:14](=[O:17])[NH:13][C:12]1=[O:18].[C:20](Cl)(=[O:24])[CH2:21][CH2:22][CH3:23].O>ClCCl>[C:20]([O:10][CH2:9][C@@H:5]1[C:6]([OH:8])([CH3:7])[C@:2]([F:1])([CH3:19])[CH:3]([N:11]2[CH:16]=[CH:15][C:14](=[O:17])[NH:13][C:12]2=[O:18])[O:4]1)(=[O:24])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 8855Butyryl chlorideHCID 68978433HCID 68978433, compound

Product 1

HCID 57867377HCID 57867377, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-((2R,4R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3,4-dimethyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (about 0.30 g, 1.09 mmol) in dichloromethane (about 5 ml) was added solution of butyroylchloride (about 0.28 ml, 2.70 mmol) in dichloromethane (about 5 ml) at about 0° C. and stirred at room temperature for overnight. Completion of the reaction monitored by thin-layer chromatography, water added to the reaction mixture and extracted with dichloromethane and the combined organic layers were washed with saturated sodium bicarbonate, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 2% methanol in dichloromethane to elude title compound (0.15 g) as a colorless solid. Yield: 40%; 1H NMR (300 MHz, CDCl3): δ 8.42 (bs, 1H), 7.39-7.35 (dd, 1H, J1=8.4 Hz, J2=8.1 Hz), 6.37 (d, 1H, J=22.8 Hz), 5.76-5.73 (dd, 1H, J1=8.4 Hz, J2=8.1 Hz), 4.58-4.52 (m, 1H), 4.39-4.37 (m, 1H), 4.26-4.20 (m, 1H), 2.68 (s, 1H), 2.38-2.33 (t, 2H), 1.69-1.61 (m, 2H), 1.48-1.25 (m, 6H), 0.99-0.94 (t, 3H); ES Mass: [M+Na]+: 367 (100%), [M+1]+ 345 (30%); IR cm−: 3504, 3147, 1725, 1677, 1560, 1180, 1086, 1062, 994; HPLC: 99%.

Workup

  1. additionadded to the reaction mixture
  2. extractionextracted with dichloromethane
  3. washthe combined organic layers were washed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4fea7cd8770c4f3c8068c14a6a1148c3
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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