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

HRID 1154443Notes

Reaction equation

HRID 1154443 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.[CH2:14]1[C@@H:17](C(O)=O)[NH:16][CH2:15]1>CS(C)=O>[Br: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 107526445-bromo-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 54191878(S)-5-bromo-1,10a-dihydroazeto[2,1-c][1,4]benzodiazepine-4,10(2H,9H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

25 g (103 mmol) of 6-bromo-isatoic acid anhydride and 10.44 g (103 mmol) of L-azetidine-2-carboxylic acid in 100 ml of dimethyl sulphoxide are stirred at 95° for 25 minutes, the dimethyl sulphoxide is removed in vacuo and the residue is heated to 150° for 3 hours in a high vacuum. By chromatography of the resulting material on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate there is obtained (S)-5-bromo-1,10a-dihydroazeto[2,1-c][1,4]benzodiazepine-4,10(2H,9H)-dione of melting point 182°-183°.

Workup

  1. customthe dimethyl sulphoxide is removed in vacuo
  2. temperaturethe residue is heated to 150° for 3 hours in a high vacuum
  3. washBy chromatography of the resulting material on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-04b63728ee274a389c37fd6e0984ea5a
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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