HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-hydroxy-cyclopent-1-enecarboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | (1R,4S)-4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl ester | HCID 68410381 | — |
| Reactant | (1R,2S)-1-amino-2-vinyl-cyclo-propane carboxylic acid tert-butyl ester | HCID 68494585 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-hydroxy-cyclopent-1-enecarboxylic acid methyl ester | HCID 59204196 | — |
Reaction Steps
To an ice cooled solution of 28 (50 mg, 37 mmol) and (1R,2S)-1-amino-2-vinyl-cyclopropane carboxylic acid tert-butyl ester in DMF (5 mL), DIPEA (47 mmol) and HATU (47 mmol) were added. After two hours the solution was concentrated and purified using column chromatography (toluene/ethyl acetate 3:1). This gave the title compound as a slightly yellow oil (50 mg, 38%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07700552B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-37845128bc9a4c409ab7813ffc4ec988 |
| Source note | uspto-grants-2010_04 |