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 917965Notes

Reaction equation

HRID 917965 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 racemic 1-(N-methylanthraniloyl)proline and 21 g. of dicyclohexylcarbonyl diimide in 300 ml. of tetrahydrofuran is stirred at room temperature for 24 hours and then heated on the steam bath for 4 hours. The reaction mixture is filtered to remove the insoluble dicyclohexyl urea and the mother liquid is concentrated to recover the desired product, which is further purified by recrystallization from ethyl acetate.

Workup

  1. additionA mixture of 24.8 g
  2. temperatureheated on the steam bath for 4 hours
  3. filtrationThe reaction mixture is filtered
  4. customto remove the insoluble dicyclohexyl urea
  5. concentrationthe mother liquid is concentrated
  6. customto recover the desired product, which
  7. customis further purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6860e4264a474dbc89fdcdd0f4faeb94
Source dataset
uspto-grants-1976_07
Patent number
US03968230

Reaction notes

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