L-Azetidine-2-carboxylic acid → HCID 54138438, compound

HRID 1378236Notes

Reaction equation

HRID 1378236 reaction equation
[Cl:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[NH:11][C:5]2=[CH:4][CH:3]=1)=O.[NH:14]1[CH2:17][CH2:16][C@H:15]1C(O)=O>CN(C)C=O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C@@H:15]3[CH2:16][CH2:17][N:14]3[C:7](=[O:9])[C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 16486L-Azetidine-2-carboxylic acidHCID 784805-Chloroisatoic anhydride

Product 1

HCID 54138438HCID 54138438, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 21926011acetic acid N,N-dimethylformamideSolvent

Procedure

59.3 g (0.3 mol) of 5-chloro-isatoic anhydride and 30.3 g (0.3 mol) of (S)-azetidine-2-carboxylic acid were suspended in 400 ml of N,N-dimethylformamide/acetic acid 5:1 and heated to 87°-90° in an oil bath under argon for 64 hrs. The solvent was removed in a vacuum and the residue was taken up in 500 ml of methanol, whereupon the mixture was stirred at room temperature for 30 min. The white, pure crystals were filtered off under suction. The solvent was removed in a vacuum and the semi-crystalline residue was recrystallized from 60 ml of methanol (hot filtration). The products were combined and dried in a vacuum. There were obtained 61.3 g (86%) of (S)-6-chloro-1,2,4,9,10,10a-hexahydro-azeto[2,1-c][1,4]benzodiazepine-4,10-dione of m.p. 229°-231° (dec.).

Workup

  1. temperatureheated to 87°-90° in an oil bath under argon for 64 hrs
  2. customThe solvent was removed in a vacuum
  3. filtrationThe white, pure crystals were filtered off under suction
  4. customThe solvent was removed in a vacuum
  5. customthe semi-crystalline residue was recrystallized from 60 ml of methanol (hot filtration)
  6. customdried in a vacuum

Sources & evidence

ORD record
ord-bd419b93a0f644f38694c4e5ed78ff1f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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