L-Proline → (S)-1,2,3,11a-tetrahydro-6-methoxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

HRID 223331Notes

Reaction equation

HRID 223331 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[NH:13][C:12](=[O:14])[O:11][C:9](=O)[C:8]=12.[NH:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1C(O)=O>CS(C)=O>[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:11])[N:15]3[CH2:22][CH2:21][CH2:20][C@H:16]3[C:12](=[O:14])[NH:13][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 145742L-ProlineHCID 107502955-Methoxy-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 54525802(S)-1,2,3,11a-tetrahydro-6-methoxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.8 g (0.025 mmol) of 6-methoxyisatoic acid anhydride and 3.0 g (0.026 mol) of L-proline in 40 ml of dimethyl sulphoxide is heated to 70° for 2 hours, the solvent is removed in a high vacuum and the oil obtained is heated to 170° for 15 minutes. After treatment with active carbon, the crude product is recrystallized from methanol, there being obtained (S)-1,2,3,11a-tetrahydro-6-methoxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione of melting point 247°-251°.

Workup

  1. customthe solvent is removed in a high vacuum
  2. customthe oil obtained
  3. temperatureis heated to 170° for 15 minutes
  4. customAfter treatment with active carbon, the crude product is recrystallized from methanol, there

Sources & evidence

ORD record
ord-277d891ef42f47e7bfffc49765bd0b69
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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