Methanol → (4R)-4-Hydroxy-L-proline methyl ester

HRID 81124

Reaction equation

HRID 81124 reaction equation
S(Cl)(Cl)=O.[OH:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH3:14]O>>[OH:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 5810L-HydroxyprolineHCID 24386Thionyl Chloride

Product 1

HCID 7015125(4R)-4-Hydroxy-L-proline methyl ester

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (270 mL) was added dropwise to methanol (1500 mL) over 1 hour, followed by the addition of (4R)-4-hydroxy-L-proline (150 g). The mixture was stirred at reflux for 36 hours, and then concentrated under reduced pressure. Methanol (1500 mL) was added, followed by a slow addition of triethylamine (310 mL). The mixture was cooled to 0° C., filtered, and the filtrate was concentrated to afford methyl (4R)-4-hydroxy-L-prolinate. The residue was used directly without further purification.

Workup

  1. temperatureat reflux for 36 hours
  2. concentrationconcentrated under reduced pressure
  3. additionMethanol (1500 mL) was added
  4. additionfollowed by a slow addition of triethylamine (310 mL)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ccbf0d3c4d19427fb2fc341df38aed51
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Linked notes

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