L-Azetidine-2-carboxylic acid → (S)-5-chloro-1,10a-dihydroazeto[2,1-c][1,4]benzodiazepine-4,10(2H,9H)-dione

HRID 1154446Notes

Reaction equation

HRID 1154446 reaction equation
[Cl: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.[CH2:14]1[C@@H:17](C(O)=O)[NH:16][CH2:15]1>CS(C)=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:10])[N:16]3[CH2:17][CH2:14][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 16486L-Azetidine-2-carboxylic acidHCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 22821768(S)-5-chloro-1,10a-dihydroazeto[2,1-c][1,4]benzodiazepine-4,10(2H,9H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

11.3 g (0.057 mol) of 6-chloro-isatoic acid anhydride and 5.78 g (0.057 mol) of L-azetidine-2-carboxylic acid are heated to 125° in 50 ml of dimethyl sulphoxide for 2 hours. The mixture is subsequently evaporated to dryness in a high vacuum and the residue obtained is heated to 150° for 2 hours. By chromatography on silica gel while eluting with ethyl acetate there is obtained (S)-5-chloro-1,10a-dihydroazeto[2,1-c][1,4]benzodiazepine-4,10(2H,9H)-dione of melting point 225°-228°.

Workup

  1. customThe mixture is subsequently evaporated to dryness in a high vacuum
  2. customthe residue obtained
  3. temperatureis heated to 150° for 2 hours
  4. washBy chromatography on silica gel while eluting with ethyl acetate

Sources & evidence

ORD record
ord-3f09c0d83b6a4e0792d58dd470853c84
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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