Methanol → HCID 44230605, compound

HRID 1516281Notes

Reaction equation

HRID 1516281 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[CH2:37][CH2:36][CH2:35][CH2:34]2)[O:12]1)(=O)C1C=CC=CC=1.CO>N>[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][CH2:36][CH2:37]1

Participants

4

Reactant 2

HCID 887MethanolHCID 57867397HCID 57867397, compound

Product 1

HCID 44230605HCID 44230605, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of ((2R,4R)-3-acetoxy-5-(6-(cyclopentylamino)-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate (about 0.31 g, 0.60 mmol) in methanolic ammonia (25% w/w 15 ml) was stirred at room temperature for overnight. Completion of the reaction monitored by thin-layer chromatography and methanol was removed under reduced pressure then 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 afford the title compound (0.2 g) as a colorless solid. Yield: 90%; 1H NMR (300 MHz, CDCl3): δ 8.33 (s, 1H), 7.92 (d, 1H, J=3.6 Hz), 6.62 (d, 1H, J=22.2 Hz), 5.83 (bs, 1H), 5.55 (s, 1H), 5.43 (bs, 1H), 4.58 (bs, 1H), 4.25-4.21 (m, 2H), 4.14-4.10 (m, 1H), 2.15-2.09 (m, 1H), 1.78-1.52 (m, 8H), 1.42-1.25 (m, 6H); ES Mass: [M+1]+ 366 (100%), 367 (45%); IR cm−: 3306, 2959, 1624, 1475, 1232, 1056, 938, 812; HPLC: 98.2%.

Workup

  1. customwas removed under reduced pressure
  2. additionwater added 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-03dc88d7a25d45e3911eba6d47bddbdd
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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