Methanol → HCID 57867352, compound

HRID 1516252Notes

Reaction equation

HRID 1516252 reaction equation
C([O:9][CH2:10][C@@H:11]1[C@@H:15]([O:16]C(=O)C2C=CC=CC=2)[C@:14]([F:26])([CH3:25])[CH:13]([O:27][CH3:28])[O:12]1)(=O)C1C=CC=CC=1.CO>N>[F:26][C@@:14]1([CH3:25])[CH:13]([O:27][CH3:28])[O:12][C@H:11]([CH2:10][OH:9])[C@H:15]1[OH:16]

Participants

4

Reactant 2

HCID 887MethanolHCID 57867359HCID 57867359, compound

Product 1

HCID 57867352HCID 57867352, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

((2R,3R,4R)-3-benzoyloxy-4-fluoro-5-methoxy-4-methyl-tetrahydrofuran-2-yl)methyl benzoate (17 g, 43.8 mmol) in methanolic ammonia solution (25% w/w, 340 ml) was stirred at room temperature for about 36 hours, completion of the reaction monitored by thin-layer chromatography, methanol was removed under reduced pressure. Water added to the reaction mixture 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 20% ethyl acetate in hexane eluded the title compound (8 g) as an off-white solid. Yield: 99%.

Workup

  1. customwas removed under reduced pressure
  2. additionWater added to the reaction mixture
  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-e733548a843a4e7390bd7f79723532c1
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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