L-Proline → HCID 56977087, compound

HRID 223328Notes

Reaction equation

HRID 223328 reaction equation
[CH2:1]([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)[CH3:2].[NH:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1C(O)=O>CS(C)=O>[CH2:1]([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)[CH3:2]

Participants

4

Reactant 2

HCID 145742L-ProlineHCID 120854096-Ethylisatoic anhydride

Product 1

HCID 56977087HCID 56977087, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

7.65 g (0.04 mol) of 6-ethylisatoic acid anhydride and 4.6 g (0.04 mol) of L-proline are suspended in 40 ml of dimethyl sulphoxide, heated to 70° for 2.5 hours, the solvent is removed in a high vacuum and the oil obtained is heated to 170° for 15 minutes. The crude product is purified by chromatography on silica gel using chloroform for the elution. There is obtained amorphous (S)-6-ethyl-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione.

Workup

  1. temperatureheated to 70° for 2.5 hours
  2. customthe solvent is removed in a high vacuum
  3. customthe oil obtained
  4. temperatureis heated to 170° for 15 minutes
  5. customThe crude product is purified by chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-81b317b17d834741bb2ff2d15d091890
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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