L-Proline → HCID 53935064, compound

HRID 1154492Notes

Reaction equation

HRID 1154492 reaction equation
[F:1][C:2]([F:16])([F:15])[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:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1C(O)=O>CS(C)=O>[F:15][C:2]([F:1])([F:16])[C:3]1[C:8]2[C:9](=[O:11])[N:17]3[CH2:24][CH2:23][CH2:22][C@H:18]3[C:12](=[O:14])[NH:13][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 145742L-ProlineHCID 127247325-(Trifluoromethyl)-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 53935064HCID 53935064, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

11.55 g (0.05 mol) of 6-(trifluoromethyl)-isatoic acid anhydride and 5.75 g (0.05 mol) of L-proline in 100 ml of dimethyl sulphoxide are heated to 70° for 1 hour, 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 methylene chloride and mixtures of methylene chloride and ethyl acetate (5%, 10%, 15%) for the elution. After recrystallization of the crude product from ethyl acetate/diethyl ether there is obtained pure (S)-1,2,3,11a-tetrahydro-6-(trifluoromethyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione of melting point 176-178°.

Workup

  1. customthe solvent is removed in a high vacuum
  2. customthe oil obtained
  3. temperatureis heated to 170° for 15 minutes
  4. customThe crude product is purified by chromatography on silica gel
  5. washfor the elution
  6. customAfter recrystallization of the crude product from ethyl acetate/diethyl ether there

Sources & evidence

ORD record
ord-b467c2e4bd6e4071abfff5462afe62b9
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

Loading…