L-Azetidine-2-carboxylic acid → HCID 53806438, compound

HRID 1154435Notes

Reaction equation

HRID 1154435 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.[CH2:14]1[C@@H:17](C(O)=O)[NH:16][CH2:15]1>CS(C)=O>[I: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 106848156-(Iodo)isatoic anhydride

Product 1

HCID 53806438HCID 53806438, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

70 g (242 mmol) of 6-iodoisatoic acid anhydride and 24.46 g (242 mmol) of L-azetidine-2-carboxylic acid in 140 ml of dimethyl sulphoxide are stirred at 105° for 2 hours, the dimethyl sulphoxide is removed in vacuo and the residue is heated to 140° in a high vacuum for 2.5 hours. By chromatography on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate there is obtained (S)-1,10a-dihydro-5-iodo-azeto[2,1-c][1,4]benzodiazepine-4,10(2H,9H)-dione of melting point 186°-187°.

Workup

  1. customthe dimethyl sulphoxide is removed in vacuo
  2. temperaturethe residue is heated to 140° in a high vacuum for 2.5 hours
  3. washBy chromatography on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-317e3562a2d94f11b76650e6521fc98a
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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