Water → HCID 86751722, compound

HRID 1939712Notes

Reaction equation

[N:1]([CH2:4][C@@H:5]([O:8][O:9][C:10]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[P:11]([OH:14])([OH:13])=[O:12])[CH2:6][OH:7])=[N+:2]=[N-:3].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(Cl)Cl>[N:1]([CH2:4][C@@H:5]([O:8][O:9][C:10]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:16])[CH3:17])[P:11]([OH:13])([OH:14])=[O:12])[CH2:6][O:7][S:29]([CH3:28])(=[O:31])=[O:30])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (R)-3-azido-2-O-(diisopropyl phosphonomethoxyl)-1,2-propanediol (6.4 g, 21.67 mmol) and triethylamine (4.39 g, 43.4 mmol) in methylene chloride (100 mL), methanesulfonylchloride (2.98 g, 26 mmol) was slowly added at 0° C. under nitrogen atmosphere. The resulting solution was stirred at 0° C. for 1 hour and then slowly warmed to room temperature during an hour. Water (100 mL) was added to the solution. The aqueous was separated and extrated with methylene chloride (150 mL×2). The combined methylene chloride extracts were dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by flash chromatography on silica gel (methylene chloride:acetone=10:1 to 3:1) to provide 7.21 g (87% yield) of the title compound as an oil.

Workup

temperatureslowly warmed to room temperature during an hour
customThe aqueous was separated
dry with materialThe combined methylene chloride extracts were dried over magnesium sulfate
customThe solvent was evaporated
customthe residue was purified by flash chromatography on silica gel (methylene chloride:acetone=10:1 to 3:1)

Sources & evidence

ORD record: ord-56743981c1824d52b905f28c706b314c
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696263

Reaction notes

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