HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-[(2-tertbutoxycarbonylaminoacetyl)amino]propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | N-Acetylcolchicinol | HCID 97865 | — |
| Reactant | 3-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)propanoic acid | HCID 21893884 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-[(2-tertbutoxycarbonylaminoacetyl)amino]propanoate | HCID 69586968 | 61% |
Reaction Steps
A mixture of N-acetyl-colchicinol (0.357 g; 1 mmol), DCCI (0.248 g; 1.2 mmol), DMAP (0.025 g; 0.2 mmol) and (7) (0.246 g; 1 mmol) in dichloromethane (7 ml) was stirred under argon atmosphere for 5 hours. After removal of the insoluble material by filtration the residue was purified by flash chromatography eluting with dichloromethane/ethanol (92/8) to give (4) as a foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07135502B1 |
| Source dataset | uspto-grants-2006_11 |
| ORD ID | ord-efb6252309a44addb99e4cf18d2c0787 |
| Source note | uspto-grants-2006_11 |