HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → Di-tert-butyl 2-(tert-butyldimethylsilyloxy)propane-1,3-diyldicarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | tert-butyl N-{3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}carbamate | HCID 375632 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | Di-tert-butyl 2-(tert-butyldimethylsilyloxy)propane-1,3-diyldicarbamate | HCID 57683620 | 86.5% |
Reaction Steps
To 29.0 g (0.1 mol) of di-tert-butyl 2-hydroxypropane-1,3-diyldicarbamate and 17.0 g (0.25 mol) of imidazole in 200 ml DMF at 0° C., was added 18.09 g (0.12 mol) of t-butyldimethylsilylchloride (TBDSMCl) in portions. The reaction was warmed up to RT and stirred for 2 hours. To this mixture was added 400 ml ether and 400 ml brine. The layers were separated and the aqueous layer was extracted with 400 ml ether. The combined organic layer was dried and concentrated to give 35 g of di-tert-butyl 2-(tert-butyldimethylsilyloxy)propane-1,3-diyldicarbamate (86% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07538223B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-562440d0eacc40aa89987591eca386e7 |
| Source note | uspto-grants-2009_05 |