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-{[(2R)-2,6-di(tertbutoxycarbonylamino)hexanoyl]amino}propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | N-Acetylcolchicinol | HCID 97865 | — |
| Reactant | 3-{[(2r)-2,6-Di(tertbutoxycarbonylamino)hexanoyl]amino}propanoic acid | HCID 54461858 | — |
| 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-{[(2R)-2,6-di(tertbutoxycarbonylamino)hexanoyl]amino}propanoate | HCID 69586384 | 32% |
Reaction Steps
A mixture of 3-{[(2R)-2,6-di(tertbutoxycarbonylamino)hexanoyl]amino}propanoic acid (2) (0.178 g; 0.5 mmol), DCCI (0.124 g; 0.6 mmol), DMAP (0.013 g; 0.1 mmol) and N-acetyl-colchicinol (0.25 g; 1.2 mmol) in dichloromethane was stirred under argon atmosphere at ambient temperature for 5 hours. After filtration of the insoluble material the residue was purified by flash chromatography eluting with dichloromethane/ethanol (95/5) to give (1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07135502B1 |
| Source dataset | uspto-grants-2006_11 |
| ORD ID | ord-114634f21c3a4a9fa0eecc265ffb4bb8 |
| Source note | uspto-grants-2006_11 |