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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1170654Erstellt: 26. Oktober 2026

Dicyclohexylcarbodiimide → Benzyl 5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate

https://huagongshe.com/reaction/1170654

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDicyclohexylcarbodiimideHCID 10868—
EduktFMOC-L-valineHCID 688217—
EduktBenzyl 4,5-dihydroxy-2-pentenoateHCID 54529065—
Katalysator4-(Dimethylamino)pyridineHCID 14284—
LösungsmittelDichloromethaneHCID 6344—
ProduktBenzyl 5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoateHCID 54039988—

Reaktionsbedingungen

Temperatur10 °C

Reaktionsschritte

A mixture of benzyl 4,5-dihydroxy-2-pentenoate (4.4 g, 20 mmole), N-FMOC-L-valine (5.8 g, 17 mmole) and DMAP (0.21 g, 1,7 mmole) in 100 ml dichloromethane was cooled to about 10° C. A solution of DCC (4.2 g, 20 mmole) in 25 ml dichloromethane was added dropwise at the same temperature and the mixture was stirred overnight at room temperature. The mixture was cooled to 5° C. and the urethane was filtered. The filtrate was evaporated under reduced pressure and the product was isolated by silica gel column chromatography.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07825238B2
Quelldatensatzuspto-grants-2010_11
ORD IDord-ae458531a48743fba13fa3d12fc2efaa
Quellennotizuspto-grants-2010_11