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

HRID 279708Notes

Reaction equation

[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]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 5810L-Hydroxyproline

Product 1

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

Procedure

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.

Workup

customthe mixture was evaporated

Sources & evidence

ORD record: ord-20a88220a2934292900890f1b6b3c541
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362341B1

Reaction notes

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