Acetone → HCID 86751718, compound

HRID 1939709Notes

Reaction equation

[CH:1]([C:4]([CH:15]([CH3:17])[CH3:16])([P:11]([OH:14])([OH:13])=[O:12])O[C@@H](C=C)CO)([CH3:3])[CH3:2].C(N([CH2:23][CH3:24])CC)C.[S:25](Cl)([CH3:28])(=[O:27])=[O:26].C(=O)(O)[O-].[Na+].C[C:36]([CH3:38])=O>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)(=O)C>[CH3:28][S:25]([CH2:36][C@H:38]([C:4]([CH:1]([CH3:2])[CH3:3])([CH:15]([CH3:16])[CH3:17])[P:11]([OH:14])([OH:13])=[O:12])[CH:23]=[CH2:24])(=[O:27])=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-2-O-(Diisopropyl phosphonomethyl)-3-butene-1,2-diol (2.62 g, 9.84 mmol) was mixed with triethylamine (1.99 g, 19.68 mmol) and 4-dimethylaminopyridine (10 mg) in 30 mL of methylene chloride. To the solution, mesyl chloride (1.35 g, 11.81 mmol) was slowly added at 0° C. The mixture was stirred at 0° C. for 30 min, then at room temperature for additional 30 min. Saturated sodium bicarbonate (50 mL) and methylen chloride (50 mL) were added. The aqueous layer was extracted with methylene chloride (75 mL×2). The combined methylene chloride extracts were dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by flash chromatography (ethyl acetate:petroleum ether=1:1 to 1:0, then ethyl acetate:acetone=5:0 to 5:1) to provide 3.27 g (97% yield) of the title compound as an oil.

Workup

waitat room temperature for additional 30 min
extractionThe aqueous layer was extracted with methylene chloride (75 mL×2)
dry with materialThe combined methylene chloride extracts were dried over magnesium sulfate
customThe solvent was evaporated
customthe residue was purified by flash chromatography (ethyl acetate

Sources & evidence

ORD record: ord-e878871a22104bd4808cbf24d172c5a1
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696263

Reaction notes

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