L-Azetidine-2-carboxylic acid → HCID 54065826, compound

HRID 1378027Notes

Reaction equation

HRID 1378027 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[C:4](=[O:10])O[C:2]1=[O:11].[CH2:12]1[C@@H:15](C(O)=O)[NH:14][CH2:13]1>CN(C)C=O.C(O)(=O)C>[S:9]1[C:5]2[C:4](=[O:10])[N:14]3[CH2:15][CH2:12][C@H:13]3[C:2](=[O:11])[NH:1][C:6]=2[CH:7]=[CH:8]1

Participants

5

Reactant 2

HCID 16486L-Azetidine-2-carboxylic acidHCID 27775521H,2H,4H-thieno(3,2-d)(1,3)oxazine-2,4-dione

Product 1

HCID 54065826HCID 54065826, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 26.9 g (171mmol) of 2H-thieno[3,2-d][1,3]oxazine-2,4(1H)-dione (EP 27214) and 16.1 g (171 mmol) of L-azetidine-2-carboxylic acid in 200 ml of dimethylformamide and 40 ml of acetic acid was stirred at 120° for 3 hours. The brown solution was evaporated and the brown residue obtained was crystallized from ethanol. There were obtained 15.2 g (43%) of (S)-6,7-dihydroazeto[1,2-a]thieno[3,2-e][1,4]diazepine-5,9(4H,5aH)-dione as a colourless crystallizate of m.p. 274°.

Workup

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

Sources & evidence

ORD record
ord-4544d8c627be44aba737450236de0d52
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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