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

HRID 1383917Notes

Reaction equation

HRID 1383917 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]O>>[ClH:1].[OH:2][C@H:3]1[CH2:7][NH:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5810L-Hydroxyproline

Product 1

HCID 114353194-Hydroxy-L-proline methyl ester hydrochlorideYield 92%

Conditions

Temperature
22 °C

Procedure

To a freshly prepared sat. solution of hydrogen chloride in methanol (100 ml) was added trans-4-hydroxy-L-proline (10.0 g, 76.26 mmol). The resulting mixture was stirred at 22° C. for 24 h, concentrated in vacuo and triturated with acetone at 0° C. Filtration afforded the title compound (12.8 g, 92%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customtriturated with acetone at 0° C
  3. filtrationFiltration

Sources & evidence

ORD record
ord-f351888097314fafa847b8f760c3f579
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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