L-Azetidine-2-carboxylic acid → HCID 54302908, compound

HRID 1154486Notes

Reaction equation

HRID 1154486 reaction equation
[F: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.[CH2:14]1[C@@H:17](C(O)=O)[NH:16][CH2:15]1>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C@@H:15]3[CH2:14][CH2:17][N:16]3[C:7](=[O:9])[C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 16486L-Azetidine-2-carboxylic acidHCID 2885605-Fluoroisatoic anhydride

Product 1

HCID 54302908HCID 54302908, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 23.7 g (0.131 mol) of 5-fluoro-isatoic acid anhydride, 13.23 g (0.131 mol) of L-azetidine-2-carboxylic acid and 150 ml of dimethyl sulphoxide is heated to 90° for 3 hours, subsequently evaporated in a high vacuum and the residue is heated in a high vacuum for 17 hours. By recrystallization from methanol there is obtained (S)-6-fluoro-1,10a-dihydroazeto[2,1-c][1,4]benzodiazepine-4,10(2H,9H)-dione of melting point 216°-217°.

Workup

  1. temperatureis heated to 90° for 3 hours
  2. customsubsequently evaporated in a high vacuum
  3. temperaturethe residue is heated in a high vacuum for 17 hours
  4. customBy recrystallization from methanol

Sources & evidence

ORD record
ord-f1b71f18bf54424089272a1cbce85f87
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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