1-[2-(Methylamino)benzoyl]-L-proline → 10-methyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

HRID 917964Notes

Reaction equation

HRID 917964 reaction equation
[CH3:1][NH:2][C:3]1[C:4](=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:5]([N:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9](O)=[O:10])=[O:6]>O1CCCC1>[CH3:1][N:2]1[C:3]2[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=2[C:5](=[O:6])[N:7]2[CH2:14][CH2:13][CH2:12][CH:8]2[C:9]1=[O:10]

Participants

3

Reactant 1

HCID 227914541-[2-(Methylamino)benzoyl]-L-proline

Product 1

HCID 985943610-methyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 24.8 g. of (-)-1-(N-methylanthraniloyl)proline and 18.0 g. of N,N'-carbonyldiimidazole in 300 ml. of dry tetrahydrofuran is stirred for 2 hours at room temperature and then heated at reflux temperature for 3 hours. The reaction mixture is concentrated to remove the solvent and the residue is extracted into benzene. The benzene solution is washed twice with water and concentrated to recover the desired product.

Workup

  1. additionA mixture of 24.8 g
  2. temperatureheated
  3. temperatureat reflux temperature for 3 hours
  4. concentrationThe reaction mixture is concentrated
  5. customto remove the solvent
  6. extractionthe residue is extracted into benzene
  7. washThe benzene solution is washed twice with water
  8. concentrationconcentrated
  9. customto recover the desired product

Sources & evidence

ORD record
ord-a9760acb26c648a18ae773d7462e2c88
Source dataset
uspto-grants-1976_07
Patent number
US03968230

Reaction notes

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