L-Azetidine-2-carboxylic acid → HCID 53904489, compound

HRID 1378118Notes

Reaction equation

HRID 1378118 reaction equation
[N:1]1[CH2:2][O:3][C:4](=[O:11])[C:5]2[C:6]=1[S:7][C:8](=O)[CH:9]=2.[CH2:12]1[C@@H:15](C(O)=O)[NH:14][CH2:13]1>CN(C)C=O.C(O)(=O)C>[S:7]1[C:6]2[NH:1][C:2](=[O:3])[C@@H:13]3[CH2:12][CH2:15][N:14]3[C:4](=[O:11])[C:5]=2[CH:9]=[CH:8]1

Participants

5

Reactant 2

HCID 16486L-Azetidine-2-carboxylic acidHCID 70076792HCID 70076792, compound

Product 1

HCID 53904489HCID 53904489, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7.23 g (42.75 mmol) of 6H-thieno[2,3-d]-[1,3]oxazine-4,6(7H)-dione (J. chem. Res. (M), 1986, 1459) and 1.99 g (24.75 mmol) of L-azetidine-2-carboxylic acid in 30 ml of dimethylformamide and 6 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 3.74 g (42%) of (S)-7,7a-dihydroazeto[1,2-a]thieno[2,3-e][1,4]diazepine-4,8(6H,9H)-dione as colourless needles of m.p. 272°-274°.

Workup

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

Sources & evidence

ORD record
ord-8a6faa138db34124b04392557a82b45b
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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