Methanol → HCID 44230460, compound

HRID 1516277Notes

Reaction equation

HRID 1516277 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:28]=[CH:27][C:26]([NH:29]C(=O)C3C=CC=CC=3)=[N:25][C:24]2=[O:38])[O:12]1)(=O)C1C=CC=CC=1.CO>N>[NH2:29][C:26]1[CH:27]=[CH:28][N:23]([C@H:13]2[C:14]([F:22])([CH3:21])[C@@:15]([OH:17])([CH3:16])[CH:11]([CH2:10][OH:9])[O:12]2)[C:24](=[O:38])[N:25]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 57867408HCID 57867408, compound

Product 1

HCID 44230460HCID 44230460, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of ((2R,4R)-3-acetoxy-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 0.22 g, 0.42 mmol) in methanolic ammonia (25% w/w 15 ml) was stirred at room temperature for overnight. Completion of the reaction mixture monitored by thin-layer chromatography and methanol was removed under reduced pressure. Water added to the crude and extracted with ethyl acetate and the organic layer was dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 15% methanol in dichloromethane to elude title compound (0.047 g). Yield: 46%; 1H-NMR: 1H NMR (300 MHz, CDCl3): δ 7.40 (dd, 1H, J1=7.5 Hz, J2=7.5 Hz), 7.25-7.17 (bs, 2H), 6.23 (d, 1H, J=23.4 Hz), 5.72 (d, 1H, J=7.5 Hz), 5.53 (s, 1H), 4.79 (t, 1H), 4.11-4.09 (m, 1H), 3.49-3.45 (m, 2H), 1.29-1.19 (m, 6H); ES Mass: [M+1]+ 274 (100%), [M+2]+ 275 (60%); IR cm−: 3459, 2927, 2855, 2274, 1635, 1028, 938, 724, 471.

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. concentrationConcentration
  6. customunder reduced pressure and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-bf8b486e1b624cff817831d124c721e4
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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