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
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | L-(+)-Cysteine | HCID 5862 | — |
| Edukt | tert-Butanol | HCID 6386 | — |
| Edukt | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Edukt | N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine | HCID 128239 | — |
| Katalysator | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | 2(R)-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionic acid tert-butyl ester | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07115769B2 |
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| Quelldatensatz | uspto-grants-2006_10 |
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| ORD ID | ord-df73c9e596ee4cf39649503178edd46d |
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| Quellennotiz | uspto-grants-2006_10 |
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