Methanol → 4-Hydroxy-L-proline methyl ester hydrochloride

HRID 2371818Notes

Reaction equation

HRID 2371818 reaction equation
Cl.CO.[C:4]([Cl:7])(=O)C.CO.[NH:10]1[CH2:18][C@H:16]([OH:17])[CH2:15][C@H:11]1[C:12]([OH:14])=[O:13]>C(OCC)C>[ClH:7].[CH3:4][O:13][C:12](=[O:14])[C@@H:11]1[CH2:15][C@@H:16]([OH:17])[CH2:18][NH:10]1

Participants

6

Reactant 4

HCID 887MethanolHCID 5810L-HydroxyprolineHCID 6367Acetyl chlorideHCID 21893726Hydrochloride methanol

Product 1

HCID 114353194-Hydroxy-L-proline methyl ester hydrochlorideYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of hydrogen chloride-methanol prepared from acetyl chloride (19 ml, 270 mmol) and methanol (170 ml) was added L-hydroxyproline (25 g, 190 mmol), and the reaction mixture refluxed for 7 hours with stirring, cooled to room temperature. The mixture was stirred at 5° C. for 1 hour after addition of diethyl ether (340 ml). The resulting precipitate was collected by filtration, washed with a solution of diethyl ether-methanol (2:1, 50 ml), and dried under nitrogen for 4 hours to afford the title compound (30.64 g, 89% yield).

Workup

  1. temperaturethe reaction mixture refluxed for 7 hours
  2. stirringThe mixture was stirred at 5° C. for 1 hour
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with a solution of diethyl ether-methanol (2:1, 50 ml)
  5. customdried under nitrogen for 4 hours

Sources & evidence

ORD record
ord-bc93c73bc8d54ac894e9c180f4b3b829
Source dataset
uspto-grants-1992_03
Patent number
US05095013

Reaction notes

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