HCID 68980616, compound → HCID 44205202, compound

HRID 1516271Notes

Reaction equation

HRID 1516271 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:24]2=[N:25][CH:26]=[N:27][C:28]=3[NH:32][CH:33]2[CH2:35][CH2:34]2)[O:12]1)(=O)C1C=CC=CC=1>O>[CH:33]1([NH:32][C:28]2[N:27]=[CH:26][N:25]=[C:24]3[C:29]=2[N:30]=[CH:31][N:23]3[CH:13]2[O:12][C@H:11]([CH2:10][OH:9])[C:15]([CH3:16])([OH:17])[C@:14]2([F:22])[CH3:21])[CH2:34][CH2:35]1

Participants

3

Reactant 1

HCID 68980616HCID 68980616, compound

Product 1

HCID 44205202HCID 44205202, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ((2R,4R)-3-acetoxy-5-(6-(cyclopropylamino)-9H-purin-9-yl)-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 0.25 g, 0.51 mmol) in methanolicammonia (25% w/w 5 ml) was stirred at room temperature for overnight. Completion of the reaction mixture monitored by thin-layer chromatography, water added to the reaction mixture and the aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine and dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 25% ethyl acetate in hexane as eluent furnished title compound (0.14 g) as a colorless gummy mass. Yield: 80%; 1H-NMR: 1H NMR (300 MHz, CDCl3): δ 8.45 (s, 1H), 8.01 (d, 1H, J=3.3 Hz), 6.60 (d, 1H, J=22.8 Hz), 6.36 (bs, 1H), 4.30-4.29 (m, 1H), 4.23-4.08 (m, 3H), 3.04 (m, 1H), 1.37 (s, 3H), 1.26 (d, 3H, J=2.4 Hz), 0.95-0.92 (m, 2H), 0.68 (m, 2H); ES Mass: [M+1]+338 (100%); IR cm−: 3512, 3055, 2933, 1745, 1384, 1113, 742, 703; HPLC: 93%.

Workup

  1. additionadded to the reaction mixture
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationConcentration
  6. customunder reduced pressure and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-e2d657d1dddf429ca83b0f124ede50ed
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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