Water → HCID 57867362, compound

HRID 1516267Notes

Reaction equation

HRID 1516267 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.[Cl:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH2:36][NH2:37].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:37][CH2:36][C:35]2[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=2[Cl:33])[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 666482-ChlorobenzylamineHCID 86634317HCID 86634317, compound

Product 1

HCID 57867362HCID 57867362, compoundYield 41%

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 0.2 g, 0.43 mmol) in ethanol (about 5 ml) was added 2-chlorobenzylamine (about 0.62 ml, 5.19 mmol) and stirred at room temperature for about 15 hours. 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 40% ethyl acetate in hexane as eluent furnished title compound (0.1 g) as a colorless gummy mass. Yield: 41%; 1H NMR (300 MHz, CDCl3): δ 8.42 (s, 1H), 8.06-7.99 (m, 3H), 7.47-7.02 (m, 7H), 6.55 (d, 1H, J=23.1 Hz), 6.28 (bs, 1H), 4.98-4.91 (m, 2H), 4.83-4.78 (m, 2H), 4.49-4.45 (m, 1H), 2.16 (s, 3H), 1.89 (d, 3H, J=2.4 Hz), 1.45 (d, 3H, J=23.1 Hz); Mass: [M+1]+ 568 (100%); IR cm−: 3414, 2931, 1751, 1619, 1276, 1230, 951, 712; HPLC: 95.2%.

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-4762f7bc2828416fb0d5dbb43fff04d4
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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