Hydrochloric Acid → Ethyl trans-4-hydroxy-L-prolinate hydrochloride
Reaktionsgleichung
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[ClH:10].[CH3:11][CH2:12]O>>[ClH:10].[CH2:11]([O:8][C:7](=[O:9])[C@@H:4]1[CH2:3][C@@H:2]([OH:1])[CH2:6][NH:5]1)[CH3:12]Komponenten
Versuchsvorschrift
Trans-4-hydroxy-L-proline was treated with EtOH and HCl gas, and the mixture was evaporated to give trans-4-hydroxy-L-proline ethyl ester hydrochloride. This product was treated with TsCl in pyridine, to give after aqueous workup N-(toluene-4-sulfonyl)-trans-4-(O-(toluene-4-sulfonyl))-L-proline ethyl ester. This product was treated with PhSH and DBU in DMF to give after aqueous workup and flash chromatography on silica gel, N-(Toluene-4-sulfonyl)-cis-4-(phenylthio)-L-proline ethyl ester. This product was treated with NaOH in CH3OH and H2O, to give after acidification, extraction, drying with MgSO4, filtration and evaporation, N-(toluene-4-sulfonyl)-cis-4-(phenylthio)-L-proline. This product was treated with HCl.Phe-OMe, BOP, and NMM in DMF, to give, after aqueous workup and flash chromatography, N-(toluene-4-sulfonyl)-cis-4-(phenylthio)-Pro-Phe-OMe. This product was treated with NaOH in CH3OH and H2O, to give, after acidification, extraction, drying with MgSO4, filtration and evaporation, the title compound as a clear oil.
Aufarbeitung
- customthe mixture was evaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-4658b915526b43b69c792eaba6c30e58
- Quelldatensatz
- uspto-grants-2003_07
- Patentnummer
- US06586602B2
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