Hydrochloric Acid → (4R)-4-Hydroxy-L-proline methyl ester

HRID 1871195Notes

Reaction equation

[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.Cl.[CH3:11]O>>[CH3:11][O:8][C:7](=[O:9])[C@@H:4]1[CH2:3][C@@H:2]([OH:1])[CH2:6][NH:5]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 5810L-Hydroxyproline

Product 1

HCID 7015125(4R)-4-Hydroxy-L-proline methyl ester

Procedure

A suspension of 4(R)-hydroxyproline (35.12 g, 267.8 mmol) in methanol (500 ml) was saturated with gaseous hydrochloric acid. The resulting solution was allowed to stand for 16 hrs and the solvent evaporated in vacuo to afford the title compound as a white solid.

Workup

customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-f9c42e275ae0413ca7f59e04e3e983fb
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103487

Reaction notes

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