Hydrochloric Acid → Ethyl trans-4-hydroxy-L-prolinate hydrochloride

HRID 1356874Notizen

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

Edukt 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 5810L-Hydroxyproline

Produkt 1

HCID 12709304Ethyl trans-4-hydroxy-L-prolinate hydrochloride

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 and Et3N in CH2Cl2, to give after aqueous workup N-(toluene-4-sulfonyl)-trans-4-hydroxy-L-proline ethyl ester. This product was treated with morpholinosulfur trifluoride in CH2Cl2, to give after aqueous workup N-(toluene-4-sulfonyl)-cis-4-fluoro-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-fluoro-L-proline. This product was treated with HCl.Phe-OBn, BOP, and NMM in DMF, to give after aqueous workup and flash chromatography the title compound as a clear oil.

Aufarbeitung

customthe mixture was evaporated

Quellen und Nachweise

ORD-Eintrag: ord-dc058d160df944bf9e3eb498818032bb
Quelldatensatz: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06586602B2

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