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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1903342Generated: November 2, 2026

Dicyclohexylcarbodiimide → BOC-Phe-(D)Trp-Lys(Z)-Thr-Cys(MBzl)-Thr-ol

https://huagongshe.com/reaction/1903342

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDicyclohexylcarbodiimideHCID 10868—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantBOC-Phe-(D)Trp-Lys(Z)-OHHCID 13391310—
ReactantH-Thr-Cys(MBzl)-Thr-ol trifluoroacetateHCID 131713418—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
ProductBOC-Phe-(D)Trp-Lys(Z)-Thr-Cys(MBzl)-Thr-olHCID 131713420—

Reaction Conditions

Temperature0 °C

Reaction Steps

2.5 ml NEt3, 11.2 g BOC-Phe-(D)Trp-Lys(Z)-OH and 4 g HOBT are added to 9 g H-Thr-Cys(MBzl)-Thr-ol trifluoroacetate in 100 ml DMF. 3.7 g DCCI in 10 ml DMF are added to the solution at -20° C. and the whole is stirred for ca. 18 hours at 0° C. and 2 hrs. at room temperature. Precipitated dicyclohexyl-urea is filtered off and the filtrate concentrated under vacuum and diluted with methanol. H2O is added until the product precipitates. The precipitate is filtered, washed with MeOH/H2O (4:1) and dried to yield the title compound:

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04435385
Source datasetuspto-grants-1984_03
ORD IDord-27760fc0223a406b9b559019cc1ffa57
Source noteuspto-grants-1984_03