Methanol → HCID 57867352, compound

HRID 1516253Notes

Reaction equation

HRID 1516253 reaction equation
C([O:9][C@H:10]1[C@:14]([F:16])([CH3:15])[CH:13]([O:17][CH3:18])[O:12][C@@H:11]1[CH2:19][OH:20])(=O)C1C=CC=CC=1.CO>N>[F:16][C@@:14]1([CH3:15])[CH:13]([O:17][CH3:18])[O:12][C@H:11]([CH2:19][OH:20])[C@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 887MethanolHCID 57867350HCID 57867350, compound

Product 1

HCID 57867352HCID 57867352, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

(2R,3R,4R)-4-fluoro-2-(hydroxymethyl)-5-methoxy-4-methyl-tetrahydrofuran-3-yl benzoate (about 18 g, 63.3 mmol) in methanolic ammonia solution (25% w/w, 360 ml) was stirred at room temperature for about 36 hours, completion of the reaction monitored by thin-layer chromatography and methanol was removed under reduced pressure. Water added to the reaction mixture and extracted with ethyl acetate, the organic layer was dried over sodium sulphate and concentrated under reduced pressure. Purification by silica gel column chromatography using 20% ethyl acetate: hexane eluded the title compound (8 g) as an off-white solid. Yield: 70%; 1H NMR (300 MHz, CDCl3): δ 4.79 (d, 1H, J=10.8 Hz), 4.01-3.97 (m, 2H), 3.85 (d, 1H,), 3.71-3.66 (m, 1H), 3.44 (s, 3H), 2.05 (brs, 1H, —OH), 2.02 (brs, 1H, —OH), 1.47 (d, 3H, J=23.4 Hz); Mass: [M+Na]+: 203 (100%); IR cm−: 3437, 3372, 3294, 2924, 1459, 1102, 1049, 1006, 821, 731.

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. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-be8a0612e03640ccb96f231ddfa1823d
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

Loading…