Hydrochloric Acid → 4-Hydroxy-L-proline methyl ester hydrochloride

HRID 1491992Notes

Reaction equation

HRID 1491992 reaction equation
[ClH:1].[OH:2][C@H:3]1[CH2:7][NH:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1.[CH3:11]COCC>CO>[ClH:1].[CH3:11][O:9][C:8](=[O:10])[C@@H:5]1[CH2:4][C@@H:3]([OH:2])[CH2:7][NH:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5810L-Hydroxyproline

Product 1

HCID 114353194-Hydroxy-L-proline methyl ester hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Anhydrous HCl was bubbled through a stirred suspension of trans-4-hydroxy-L-proline (80 g, 0.61 mol) in 500 ml anhydrous methanol until the mixture was homogeneous. The reaction was heated to reflux for five hours, and the volume of the solvent then reduced by one half. Ether (100 ml) was added, and the mixture kept in a freezer overnight. The resulting precipitate was filtered, washed with ether and dried under reduced pressure to yield 111 g of present title product (93% yield). mp 170°-172° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for five hours
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-243a265df2d74636945429c5af02036a
Source dataset
uspto-grants-1994_12
Patent number
US05371235

Reaction notes

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