Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | tert-butyl ((3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl)carbamate | HCID 66989555 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86659127 | HCID 86659127 | — |
Reaction Steps
Methanesulfonyl chloride (30 ml) in DCM (100 ml) was added dropwise to a solution of 1,5-an hydro-2,4-dideoxy-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-L-threo-pentitol (75 g) and triethylamine (58 ml) in DCM (900 ml) at 0° C., maintaining the temperature below 3° C. during the addition. The mixture was stirred for 30 min, warmed to 25° C. and stirred for 2 h. The reaction mixture was washed with water (2×1.4 l), the organic phase dried and the solvent evaporated to give 1,5-anhydro-2,4-dideoxy-2-({[(1,1-dimethylethy)oxy]carbonyl}amino)-3-O-(methylsulfonyl)-L-threo-pentitol (103.1 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08470835B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-80aa212dd8904463bd4c80af9f5b7678 |
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| Source note | uspto-grants-2013_06 |
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