Methanol → HCID 57867359, compound

HRID 1516251Notes

Reaction equation

HRID 1516251 reaction equation
[C:1]([O:9][CH2:10][C@@H:11]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@:14]([F:26])([CH3:25])[CH:13]([OH:27])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28]O>>[C:1]([O:9][CH2:10][C@@H:11]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@:14]([F:26])([CH3:25])[CH:13]([O:27][CH3:28])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 56605060HCID 56605060, compound

Product 1

HCID 57867359HCID 57867359, compoundYield 56.2%

Conditions

Temperature
80 °C

Procedure

To a stirred solution of ((2R,3R,4R)-3-benzoyloxy-4-fluoro-5-hydroxy-4-methyl-tetrahydrofuran-2-yl)methyl benzoate (about 60 g, 160 mmol) in methanol (about 300 ml), boron trifluoro etherate (about 60.02 ml, 481 mmol) was added at room temperature then reaction mixture was heated to about 80° C. for about 5 hours. After that the reaction was quenched with saturated sodium bicarbonate solution, methanol was removed under reduced pressure, extracted with ethyl acetate. The combined organic extracts were washed with water, brine and dried over sodium sulphate. The organic layer was removed under reduced pressure and the residue was purified by silica gel column chromatography using 8% ethyl acetate: hexane as eluent furnished title compound A (17 g), and 15% ethyl acetate eluded title compound B (18 g) as a colorless liquid. Yield: Combined yield: 56.2%; Intermediate A: 1H NMR (300 MHz, CDCl3) compound D: δ 8.01-7.93 (m, 4H), 7.56-7.48 (m, 6H), 5.53 (dd, 1H, J=24.3 Hz, 7.80 Hz), 4.97 (d, 1H, J=9.6 Hz), 4.58-4.53 (m, 2H), 4.41-4.38 (m, 1H), 3.30 (s, 3H), 1.44 (d, 3H, J=22.8); Mass: [M+Na]+: 413 (80%), [M-OCH3]+:357.19 (100%); IR cm−: 3439, 2961, 2939, 1728, 1602, 1452, 1270, 1117, 710.

Workup

  1. customreaction mixture
  2. customAfter that the reaction was quenched with saturated sodium bicarbonate solution, methanol
  3. customwas removed under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over sodium sulphate
  7. customThe organic layer was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-68f9f69d521649ffaf8767696636bade
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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