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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1277397Generated: October 30, 2026

Dicyclohexylcarbodiimide → HCID 131712284, compound

https://huagongshe.com/reaction/1277397

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDicyclohexylcarbodiimideHCID 10868—
Reactant3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 89529—
ReactantGlycine tert-butyl esterHCID 151417—
ReactantZ-D-Thr-OHHCID 853484—
SolventTetrahydrofuranHCID 8028—
ProductHCID 131712284HCID 13171228469.1%

Reaction Steps

In 50 ml of THF are dissolved 5.0 g of Z-(D)-Thr-OH and 3.6 g of H-Gly-OBut. After cooling, 3.9 g of HONB and 4.5 g of DCC are added, and the mixture is stirred overnight. The solvent is distilled off, and the residue is extracted with 100 ml of AcOEt, followed by washing with water and drying over anhydrous sodium sulphate. The AcOEt is distilled off, and the residue is treated with petroleum ether. Recrystallization from AcOEt-petroleum ether yields 5.0 g of the desired compound. m.p. 56°-57° C., [α]D23 +13.8° (c=0.5, MeOH), Rf1 =0.69.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04277394
Source datasetuspto-grants-1981_07
ORD IDord-fa8911d41a0d4cfe9c9b18dd77cd9ea5
Source noteuspto-grants-1981_07