L-Proline → HCID 53984680, compound

HRID 1154437Notes

Reaction equation

HRID 1154437 reaction equation
[I: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>[I: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 106848156-(Iodo)isatoic anhydride

Product 1

HCID 53984680HCID 53984680, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

14.6 g (0.050 mol) of 6-iodo-isatoic acid anhydride and 6.6 g (0.058 mol) of L-proline in 50 ml of dimethyl sulphoxide are heated to 70° for 30 minutes, 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 a mixture of methylene chloride and ethyl acetate for the elution. There is obtained (S)-1,2,3,11a-tetrahydro-6-iodo-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione which melts at 212°-215° after recrystallization from methanol.

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. additiona mixture of methylene chloride and ethyl acetate
  6. washfor the elution

Sources & evidence

ORD record
ord-1291a06561d24847bc997c2af596bbf4
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

Loading…