Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2,6-Lutidine | HCID 7937 | — |
| Reactant | Triisopropylsilyl trifluoromethanesulfonate | HCID 2724529 | — |
| Reactant | HCID 58941864 | HCID 58941864 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58941848 | HCID 58941848 | 87% |
Reaction Steps
To a solution of methyl 5-(hydroxymethyl)-1,2,3-thiadiazole-4-carboxylate (1.22 g, 0.007 mol) in DCM (20 mL) at 0° C. was added 2,6-lutidine (2.0 mL, 0.018 mol) followed by triisopropylsilyl triflate (2.4 mL, 0.0091 mol). The solution was stirred at 0° C. for 5 minutes. The reaction was then concentrated and purified by flash chromatography to give the desired product (2.0 g, 87%). 1H NMR (400 MHz, CDCl3): δ; MF═C14H26N2O3SSi; LCMS calculated for C14H27N2O3SSi (M+H)+: m/z=331.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08450351B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-8a6f0473b32741c5bad7f6df61b64715 |
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| Source note | uspto-grants-2013_05 |
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