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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 720932Generated: October 25, 2026

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

https://huagongshe.com/reaction/720932

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDicyclohexylcarbodiimideHCID 10868—
ReactantN-AcetylcolchicinolHCID 97865—
Reactant3-{[(2r)-2,6-Di(tertbutoxycarbonylamino)hexanoyl]amino}propanoic acidHCID 54461858—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventDichloromethaneHCID 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}propanoateHCID 6958638432%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07135502B1
Source datasetuspto-grants-2006_11
ORD IDord-114634f21c3a4a9fa0eecc265ffb4bb8
Source noteuspto-grants-2006_11