HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbamimidic acid, N,N'-bis(1-methylethyl)-, 1-methylethyl ester → tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbamimidic acid, N,N'-bis(1-methylethyl)-, 1-methylethyl ester | HCID 11332901 | — |
| Reactant | tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-carboxy-ethenyl]cyclopropane-carboxylate | HCID 12807775 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate | HCID 86739004 | 33% |
Reaction Steps
2 g of O-isopropyl-N,N'-diisopropyl-isourea were added to a mixture of 2.7 g of the product of Step A and 10 ml of ethyl acetate and the mixture was stirred at room temperature for one hour, refluxed for 90 minutes and then cooled to 20° C. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The 3.5 g of oil residue were chromatographed over silica gel and eluted with a 7-3 benzene-cyclohexane mixture to obtain 1 g of tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate which was used as is for the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04547522 |
| Source dataset | uspto-grants-1985_10 |
| ORD ID | ord-b8b1581900384123aa92dcf9829164f4 |
| Source note | uspto-grants-1985_10 |