HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropanecarbonyl chloride → 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropanecarbonyl chloride | HCID 77637 | — |
| Reactant | 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester | HCID 67280748 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester | HCID 67282301 | 99.5% |
Reaction Steps
A solution of 27 (500 mg, 1.22 mmol) in DCM (10 mL) was cooled to 0° C. and treated with TEA (0.26 mL, 1.83 mmol) and cyclopropanecarbonyl chloride (0.13 mL, 1.46 mmol). After 2 h, the reaction mixture was diluted with DCM, washed successively with 1M HCl, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 44 (580 mg) as a pale yellow-colored foam that was used without further purification. Mass spectrum, m/z [478.6] (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08481495B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-9607fb9ca73d467ea7d81e9a1b6be7c6 |
| Source note | uspto-grants-2013_07 |