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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1242845Erstellt: 24. Oktober 2026

L-(+)-Cysteine → 2(R)-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionic acid tert-butyl ester

https://huagongshe.com/de/reaction/1242845

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktL-(+)-CysteineHCID 5862—
Edukttert-ButanolHCID 6386—
EduktDicyclohexylcarbodiimideHCID 10868—
EduktN-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteineHCID 128239—
Katalysator4-(Dimethylamino)pyridineHCID 14284—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt2(R)-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionic acid tert-butyl esterHCID 11467857—

Reaktionsschritte

In one incarnation of the present invention, as illustrated below, the cysteine derivative is 2(R)-(benzhydrylidene-amino)-3-tritylsulfanyl-propionic acid tert-butyl ester. 2(R)-(Benzhydrylidene-amino)-3-tritylsulfanyl-propionic acid tert-butyl ester can be formed by the following process: (1) 2(R)-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (i.e., (R)-cysteine with Fmoc a protected amino group and with a trityl protected —SH group), is reacted with t-butyl alcohol and dicyclohexyl carbodiimide (DCC) in 4-(dimethylamino)pyridine (DMAP) and tetrahydrofuran (THF) at room temperature to form 2(R)-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionic acid tert-butyl ester; (2) the Fmoc group is removed from the 2(R)-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionic acid tert-butyl ester using either diethylamine in dichloromethane or piperidine in dichloromethane to form 2(R)-amino-3-tritylsulfanyl-propionic acid tert-butyl ester; and (3) the 2(R)-amino-3-tritylsulfanyl-propionic acid tert-butyl ester is reacted with benzhydrylideneamine in dichloromethane at room temperature to form 2(R)-(benzhydrylidene-amino)-3-tritylsulfanyl-propionic acid tert-butyl ester.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07115769B2
Quelldatensatzuspto-grants-2006_10
ORD IDord-df73c9e596ee4cf39649503178edd46d
Quellennotizuspto-grants-2006_10