Water → HCID 57867393, compound

HRID 1516264Notes

Reaction equation

HRID 1516264 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.[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH2:38][NH2:39].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:39][CH2:38][C:37]2[CH:40]=[CH:41][CH:42]=[C:35]([O:34][CH3:33])[CH:36]=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 211563-MethoxybenzylamineHCID 86634317HCID 86634317, compound

Product 1

HCID 57867393HCID 57867393, compoundYield 21%

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 0.4 g, 0.86 mmol) in ethanol (about 5 ml) was added 3-methoxybenzylamine (about 1.34 ml, 10.38 mmol) and refluxed for about 20 minutes. Completion of the reaction 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 (0.10 g) as a colorless gummy mass. Yield: 21%; 1H NMR (300 MHz, CDCl3): δ 8.42 (s, 1H), 8.03-7.98 (m, 3H), 7.60-7.42 (m, 3H), 6.99-6.94 (m, 2H), 6.84-6.81 (m, 2H), 6.55 (d, 1H, J=23.1 Hz), 6.31 (bs, 1H), 4.84-4.78 (m, 3H), 4.49-4.45 (m, 1H), 3.79 (s, 3H), 2.18 (s, 3H), 1.89 (d, 3H, J=2.4 Hz), 1.47 (d, 3H, J=23.1 Hz); Mass: [M+1]+ 564 (100%), [M+Na]+ 586 (40%); IR cm−: 3430, 2928, 2381, 2170, 1734, 1624, 1461, 1053, 950, 713; HPLC: 90.1%.

Workup

  1. temperaturerefluxed for about 20 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-5e580b79421e4a73922a96a7d8615c2a
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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