Water → HCID 57867397, compound

HRID 1516272Notes

Reaction equation

HRID 1516272 reaction equation
[C:1]([O:9][CH2:10][C@@H:11]1[C:15]([O:17][C:18](=[O:20])[CH3:19])([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]=3Cl)[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:33]1([NH2:38])[CH2:37][CH2:36][CH2:35][CH2:34]1.O>C(O)C>[C:1]([O:9][CH2:10][C@@H:11]1[C:15]([O:17][C:18](=[O:20])[CH3:19])([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:38][CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2906CyclopentylamineHCID 86634317HCID 86634317, compound

Product 1

HCID 57867397HCID 57867397, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ((2R,4R)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 0.50 g, 1.08 mmol) in ethanol (about 5 ml) was added cyclopentylamine (about 1.28 ml, 12.9 mmol) and refluxed for about 30 minutes. 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 6% methanol in dichloromethane as eluent furnished title compound (0.42 g) as a colorless solid. Yield: 76%; 1H-NMR: 1H NMR (300 MHz, CDCl3): δ 8.39 (s, 1H), 8.06-7.96 (m, 3H), 7.57-7.42 (m, 3H), 6.54 (d, 1H, J=23.1 Hz), 5.92 (d, 1H, J=7.5 Hz), 4.83-4.77 (m, 2H), 4.48-4.44 (m, 1H), 2.15 (s, 3H), 2.08-1.91 (m, 1H), 1.89-1.88 (d, 3H, J=2.1 Hz), 1.78-1.58 (m, 8H), 1.44 (d, 3H, J=23.1 Hz); ES Mass: [M+1]+ 526 (20%), [M+Na] 548 (100%); IR cm−: 3437, 2925, 2855, 1733, 1612, 1232, 1059, 951, 711; HPLC: 98%.

Workup

  1. temperaturerefluxed for about 30 minutes
  2. additionadded to the reaction mixture
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationConcentration
  7. customunder reduced pressure and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-b41f3e362c7b4e879d52005fd8f7e2e9
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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