Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 57099433 | HCID 57099433 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 54208445 | HCID 54208445 | 100.2% |
Reaction Steps
A solution of (2R,3R)-O-benzyl-2-tert-butoxycarbonylamino-3-[N-(2-methanesulfonyloxyethyl)-N-methanesulfonylamino]butanol (2.6 g) in dry DMF (15 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 189 mg) in dry DMF (10 ml) at 4° C. over 20 minutes. The mixture was stirred at same temperature for 45 minutes and then poured into a mixture of ice and 1N HCl (8 ml). The mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4 and concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent: AcOEt in n-hexane 40% and 50%) to give 2.1 g of (2R,3R)-2-benzyloxymethyl-1-tert-butoxycarbonyl-4-methanesulfonyl-3-methylpiperazine as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06333324B1 |
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| Source dataset | uspto-grants-2001_12 |
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| ORD ID | ord-78b5e86c512e4a21b90fc5277bcb29da |
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| Source note | uspto-grants-2001_12 |
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