Acetic Acid → HCID 54223915, compound

HRID 903434Notes

Reaction equation

HRID 903434 reaction equation
[C:1]([CH2:9][CH:10]([CH3:21])[C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[Br:26]Br.CCCCCC>ClCCl>[C:1]([CH:9]([Br:26])[CH:10]([CH3:21])[C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 8058HexaneHCID 24408BromineHCID 54210062HCID 54210062, compound

Product 1

HCID 54223915HCID 54223915, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1.25 g. of 1-(3-benzoyl-2-methylpropionyl)-L-proline (isomer A of Example 9) in 30 ml. of acetic acid, is added 0.7 g. of bromine in 10 ml. of acetic acid. The mixture is stirred at room temperature for 18 hours, the solvent is concentrated in vacuo to 1/2 volume and the mixture is poured into ice and water. This mixture is extracted with dichloromethane. The organic extract is washed with water, then sodium chloride solution, dried over magnesium sulfate and the solvent is removed in vacuo giving a gum. This gum is dissolved in dichloromethane, hexane is added and the solvent is removed at room temperature giving a white glass. This glass is chromatographed on a silica gel column with ethyl acetate-hexane-acetic acid (75:25:2) giving 1.25 g. of the desired product as a white glass (3-bromo derivative of isomer A).

Workup

  1. additionTo a mixture of 1.25 g
  2. concentrationthe solvent is concentrated in vacuo to 1/2 volume
  3. additionthe mixture is poured into ice and water
  4. extractionThis mixture is extracted with dichloromethane
  5. extractionThe organic extract
  6. washis washed with water
  7. dry with materialsodium chloride solution, dried over magnesium sulfate
  8. customthe solvent is removed in vacuo
  9. customgiving a gum
  10. customthe solvent is removed at room temperature
  11. customgiving a white glass
  12. customThis glass is chromatographed on a silica gel column with ethyl acetate-hexane-acetic acid (75:25:2)
  13. customgiving 1.25 g

Sources & evidence

ORD record
ord-022735ae94074e4c8c0cec5780835eca
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

Loading…