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

HRID 223324Notes

Reaction equation

HRID 223324 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=[O:13])[O:10][C:8](=O)[C:7]=12.[NH:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1C(O)=O>CS(C)=O>[Br:1][C:2]1[C:7]2[C:8](=[O:10])[N:14]3[CH2:21][CH2:20][CH2:19][C@H:15]3[C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 145742L-ProlineHCID 107526445-bromo-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 22821785(S)-6-bromo-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

9.2 g (0.038 mol) of 6-bromoisatoic acid anhydride and 4.6 g (0.040 mol) of L-proline in 55 ml of dimethyl sulphoxide are heated at 70° for 1 hour, the solvent is removed in a high vacuum and the oil obtained is heated at 170° for 15 minutes. The crude product is purified by chromatography on silica gel using a mixture of chloroform and methanol (20:1) as the elution agent. There is obtained (S)-6-bromo-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione which melts at 221°-224° after recrystallization from chloroform/hexane.

Workup

  1. customthe solvent is removed in a high vacuum
  2. customthe oil obtained
  3. temperatureis heated at 170° for 15 minutes
  4. customThe crude product is purified by chromatography on silica gel using
  5. additiona mixture of chloroform and methanol (20:1) as the elution agent

Sources & evidence

ORD record
ord-dfdf3ddaf72940bea147aeb8c42646f0
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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