Methanol → HCID 44230606, compound

HRID 1516282Notes

Reaction equation

HRID 1516282 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[CH2:38][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][CH2:38]1

Participants

4

Reactant 2

HCID 887MethanolHCID 57867403HCID 57867403, compound

Product 1

HCID 44230606HCID 44230606, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of ((2R,4R)-3-acetoxy-5-(6-(cyclohexylamino)-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate (about 0.32 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 elude title compound (0.2 g) as a colorless solid. Yield: 86%; 1H NMR (300 MHz, CDCl3): δ 8.32 (s, 1H), 7.93 (d, 1H, J=3.3 Hz), 6.60 (d, 1H, J=22.5 Hz), 5.79 (bs, 1H), 5.51 (s, 1H), 5.23 (bs, 1H), 4.25-4.13 (m, 3H), 2.17-2.04 (m, 1H), 1.76-1.52 (m, 16H); ES Mass: [M+1]+ 380 (100%), 381 (45%); IR cm−: 3338, 2928, 2854, 1624, 1475, 1226, 1062, 938, 740; HPLC: 97.8%.

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-28fd3620205f481d81d38635c196e409
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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