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

HRID 1292681Notes

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 gasseous 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-1c66f17bb44b4840894b92e90da55183
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05756528

Reaction notes

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