Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | (4S)-4-(hydroxymethyl)-1,3-oxazolidin-2-one | HCID 14456890 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 15759629 | HCID 15759629 | 96.2% |
Reaction Steps
Under atmosphere of argon, a solution of (4S)-4-(hydroxymethyl)-1,3-oxazolidine-2-one (34.1 g) in N,N-dimethylformamide (300 mL) was added by imidazole (25.7 g) and was cooled down to the temperature of 0° C. To the mixture, a solution of tert-butyldimethylsilylchloride (48.2 g) in N,N-dimethylformamide (300 mL) was moderately dropped and the mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate and water and was washed with saturated brine. The organic layer was dried over an anhydrous magnesium sulfate and concentrated to give the title compound (64.8 g) having the following physical data, which was used for the next reaction without purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07256211B1 |
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| Source dataset | uspto-grants-2007_08 |
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| ORD ID | ord-25b055b04d524c94875f2eebe8b81086 |
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| Source note | uspto-grants-2007_08 |
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