Methanol → HCID 135978870, compound

HRID 1516287Notes

Reaction equation

HRID 1516287 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:31]=[N:30][C:29]3[C:28](=[O:32])[NH:27][CH:26]=[N:25][C:24]2=3)[O:12]1)(=O)C1C=CC=CC=1.CO>N>[F:22][C@:14]1([CH3:21])[C:15]([OH:17])([CH3:16])[C@@H:11]([CH2:10][OH:9])[O:12][CH:13]1[N:23]1[CH:31]=[N:30][C:29]2[C:28](=[O:32])[NH:27][CH:26]=[N:25][C:24]1=2

Participants

4

Reactant 2

HCID 887MethanolHCID 135978869HCID 135978869, compound

Product 1

HCID 135978870HCID 135978870, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To a solution of ((2R,4R)-3-acetoxy-4-fluoro-3,4-dimethyl-5-(6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-2-yl)methyl benzoate (about 0.30 g, 0.67 mmol) in methanolic ammonia (25% w/w, 10 ml) was stirred at room temperature for overnight. Completion of the reaction monitored by thin-layer chromatography, methanol was removed under reduced pressure, water added to the crude and extracted with ethyl acetate. The organic layer was dried over sodium sulphate, concentrated under reduced pressure and purified by silica gel column chromatography using 5% methanol in dichloromethane to elude title compound (0.07 g) as a colorless solid. Yield: 35%; 1H NMR (300 MHz, CD3OD): δ 8.14 (d, 1H, J=3.6 Hz), 8.06 (s, 1H), 6.41 (d, 1H, J=21.9 Hz), 4.43-4.40 (m, 1H), 3.88-3.83 (m, 2H), 1.38-1.28 (m, 6H); Mass: [M+1]+ 299 (100%), [M+Na]+321 (30%); HPLC: 95.2%.

Workup

  1. customwas removed under reduced pressure, water
  2. additionadded to the crude
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-8a8e7c6b5de84c459a4e2b3d89abd49e
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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