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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1600123Generated: October 26, 2026

Dicyclohexylcarbodiimide → 4-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythropentonoyl)-1-piperazinecarboxylic acid phenylmethyl ester

https://huagongshe.com/reaction/1600123

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDicyclohexylcarbodiimideHCID 10868—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantBenzyl piperazine-1-carboxylateHCID 643495—
Reactant2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythro-pentonic acidHCID 67648725—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventDichloromethaneHCID 6344—
Product4-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythropentonoyl)-1-piperazinecarboxylic acid phenylmethyl esterHCID 13171985557.4%

Reaction Steps

A mixture of 0.941 g of product from Example 150, 0.652 g of 1-hydroxybenzotriazole, 1.17 g of 1-benzyloxycarbonyl piperazine, 1.39 g of dicyclohexylcarbodiimide and 8 ml of dry methylene chloride is stirred at room temperature for 1 hour. Five ml of dimethylformamide is added and the stirring continued overnight at room temperature. The reaction mixtureis diluted with water and extracted with chloroform. The organic layer is dried, concentrated in vacuo and the residue purified by chromatography (silica gel: 10-80% ethyl acetate/hexane) to give 1.1 g of the desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05744465
Source datasetuspto-grants-1998_04
ORD IDord-160bf50d7617478ba2908728ccebf0e4
Source noteuspto-grants-1998_04