Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 86751721 | HCID 86751721 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86751722 | HCID 86751722 | 87% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05696263 |
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| Source dataset | uspto-grants-1997_12 |
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| ORD ID | ord-56743981c1824d52b905f28c706b314c |
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| Source note | uspto-grants-1997_12 |
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