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

HRID 1741486Notes

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-2bd27c9a5d2e4399b748009c2accb232
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972984

Reaction notes

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