L-Azetidine-2-carboxylic acid → HCID 54194909, compound

HRID 1378119Notes

Reaction equation

HRID 1378119 reaction equation
[F:1][C:2]1[C:7]2[C:8](=[O:13])O[C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:14]1[C@@H:17](C(O)=O)[NH:16][CH2:15]1>CN(C)C=O.C(O)(=O)C>[F:1][C:2]1[C:7]2[C:8](=[O:13])[N:16]3[CH2:17][CH2:14][C@H:15]3[C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 16486L-Azetidine-2-carboxylic acidHCID 27830576-Fluoroisatoic anhydride

Product 1

HCID 54194909HCID 54194909, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 10 g (55.2 mmol) of 5-fluoro-2H-3,1-benzoxazine-2,4(1H)-dione and 5.66 g (55.2 mmol) of L-azetidine-2-carboxylic acid in 75 ml of dimethylformamide and 15 ml of acetic acid was stirred at 120° for 16 hours. The brown solution was evaporated and the brown residue obtained was crystallized from ethanol. There were obtained 6 g (42%) of (S)-5-fluoro-1,2,4,9,10,10a-hexahydroazeto[2,1-c][1,4]benzodiazepine-4,10-dione as beige needles of m.p. 232°-233.5°.

Workup

  1. customThe brown solution was evaporated
  2. customthe brown residue obtained
  3. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-1a5403ef4f2046c9a1988e7dd75f95c3
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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