Methanol → HCID 86592632, compound

HRID 1244551Notes

Reaction equation

HRID 1244551 reaction equation
[OH:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[CH2:12][CH:11]([C:15]([OH:17])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1.[CH3:18]O>S(=O)(=O)(O)O.COC(OC)(C)C>[CH3:18][O:16][C:15]([CH:11]1[CH2:12][C:13](=[O:14])[N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][OH:1])=[CH:8][CH:7]=2)[CH2:10]1)=[O:17]

Participants

5

Reactant 2

HCID 887MethanolHCID 21920055HCID 21920055, compound

Product 1

HCID 86592632HCID 86592632, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

In a 10 14-necked flask equipped with a reflux condenser, a thermometer, and a mechanical stirrer, the crude (RS)-1-(4-hydroxyoxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid is dissolved in a mixture of 5000 ml of methanol, 24 ml of concentrated sulfuric acid and 400 ml of 2,2-dimethoxypropane and stirred under reflux during 2 h. For the working-up, the reaction solution is reduced to half of its volume by distillation, then transferred into a 20 l vessel. Under stirring at 40° C., a mixture of 2500 ml of water/ice (1:1) is added. Crystallisation started immediately, and, thereupon, the fine white crystals are collected on a filter funnel. They are washed with total 2000 ml of cold water until the filtrate, at the beginning brownish-rose, becomes colorless and neutral. The well pressed and pre-dried product from the filter funnel is dried under reduced pressure to yield 980 g (84% of theory, 2 steps) of the (RS)-1-(4-hydroxyoxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester as a white solid; MS: m/e=234 (M+H)+.

Workup

  1. customIn a 10 14-necked flask equipped with a reflux condenser
  2. temperatureunder reflux during 2 h
  3. distillationthe reaction solution is reduced to half of its volume by distillation
  4. customtransferred into a 20 l vessel
  5. stirringUnder stirring at 40° C.
  6. additiona mixture of 2500 ml of water/ice (1:1)
  7. additionis added
  8. customCrystallisation
  9. customthe fine white crystals are collected on a filter funnel
  10. washThey are washed with total 2000 ml of cold water until the filtrate
  11. custompre-dried product from the filter funnel is dried under reduced pressure

Sources & evidence

ORD record
ord-10e636f02ec84713b07f644d056ce5e4
Source dataset
uspto-grants-2006_10
Patent number
US07122562B2

Reaction notes

Loading…