Ethanol → HCID 53988049, compound

HRID 903436Notes

Reaction equation

HRID 903436 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:9](=[O:12])(O)[O-].[Na+].O.[CH2:15]([OH:17])[CH3:16].CCO[CH2:21][CH3:22]>ClCCl>[C:15]([CH2:21][CH2:22][C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:12])(=[O:17])[C:16]1[CH:8]=[CH:7][CH:6]=[CH:2][CH:3]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 962WaterHCID 3283Diethyl EtherHCID 145742L-ProlineHCID 516892Sodium Bicarbonate

Product 1

HCID 53988049HCID 53988049, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 25.5 g. of L-proline and 37.3 g. of sodium bicarbonate in 800 ml. of water is added a slurry of 61.0 g. of 3-benzoylpropionic acid hydroxysuccinimide ester (Example 15) in 800 ml. of ethanol. The mixture is concentrated to 1/2 volume, cooled and acidified with concentrated hydrochloric acid. The mixture is extracted with dichloromethane and the extract washed with water, saturated sodium chloride and dried over magnesium sulfate. The solvent is removed under vacuum to give an orange gum which is rubbed to a solid with ether containing a little dichloromethane. This solid is recrystallized from 250 ml. of acetone by displacing with hexane. Cooling for 2 hours gives 32.6 g. of the desired product as white crystals, m.p. 95°-97° C.

Workup

  1. concentrationThe mixture is concentrated to 1/2 volume
  2. temperaturecooled
  3. extractionThe mixture is extracted with dichloromethane
  4. washthe extract washed with water, saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is removed under vacuum
  7. customto give an orange gum which
  8. customThis solid is recrystallized from 250 ml
  9. temperatureCooling for 2 hours
  10. customgives 32.6 g

Sources & evidence

ORD record
ord-9dd016a1b4cc4159a7942c51be7df66d
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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