Methanol → Methyl 5-oxo-L-prolinate

HRID 55115

Reaction equation

HRID 55115 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:14]O>>[CH3:14][O:8][C:7](=[O:9])[C@@H:2]1[CH2:3][CH2:4][C:5](=[O:6])[NH:1]1

Participants

4

Reactant 3

HCID 887MethanolHCID 7405L-Pyroglutamic AcidHCID 24386Thionyl Chloride

Product 1

HCID 78646Methyl 5-oxo-L-prolinate

Conditions

Temperature
0 °C

Procedure

L-Pyroglutamic acid (15.17 g, 0.1175 mol) was dissolved in CH3OH (100 mL), cooled to 0° C. under Ar and treated dropwise with thionyl chloride (18.9 mL, 0.259 mol) with stirring. The bath was removed and stirring was continued at ambient temperature for 3.5 h. Water (150 mL) and solid NaHCO3 (60 g) were added, the CH3OH was removed on a rotary evaporator, and the residue extracted with CH2Cl2 (3×150 mL). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to dryness to give the title compound.

Workup

  1. customThe bath was removed
  2. stirringstirring
  3. additionWater (150 mL) and solid NaHCO3 (60 g) were added
  4. customthe CH3OH was removed on a rotary evaporator
  5. extractionthe residue extracted with CH2Cl2 (3×150 mL)
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4d59c37e20d84a41aea1bc6a4182c2d8
Source dataset
uspto-grants-1997_04
Patent number
US05624936

Linked notes

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