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

HRID 223336Notes

Reaction equation

HRID 223336 reaction equation
[CH2:1]1[C@@H:4]([C:5]([OH:7])=O)[NH:3][CH2:2]1.[CH3:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[NH:19]C(=O)O[C:15](=[O:16])[C:14]=12>CS(C)=O>[CH3:8][C:9]1[C:14]2[C:15](=[O:16])[N:3]3[CH2:2][CH2:1][C@H:4]3[C:5](=[O:7])[NH:19][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 16486L-Azetidine-2-carboxylic acidHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 22839900(S)-1,10a-dihydro-5-methyl-2H-azeto[2,1-c][1,4]benzodiazepine-4,10(9H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

13.0 g (128.4 mmol) of L-azetidine-2-carboxylic acid and 22.7 g (128.4 mmol) of 6-methylisatoic acid anhydride in 150 ml of dimethyl sulphoxide are heated to 95° for 3 hours, evaporated to dryness in a high vacuum and the residue obtained is heated to 140° for 2.25 hours. By crystallization from ethyl acetate there is obtained (S)-1,10a-dihydro-5-methyl-2H-azeto[2,1-c][1,4]benzodiazepine-4,10(9H)-dione of melting point 159°-160°.

Workup

  1. customevaporated to dryness in a high vacuum
  2. customthe residue obtained
  3. temperatureis heated to 140° for 2.25 hours
  4. customBy crystallization from ethyl acetate

Sources & evidence

ORD record
ord-413f278545da43f0a08033f5e8debf57
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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