Bis-(1H-imidazol-2-YL)-methanone → [2-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid methyl ester

HRID 1592022Notes

Reaction equation

HRID 1592022 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=O.[S:13]([N:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH2:18][C:19](O)=[O:20])(=[O:16])(=[O:15])[NH2:14]>C1COCC1>[CH3:32][O:31][C:29](=[O:30])[CH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:17]1[CH2:18][C:19](=[O:20])[NH:14][S:13]1(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 67138346N-sulfamoyl-N-[2-(methoxycarbonylmethyl)-phenyl]glycine

Product 1

HCID 58997412[2-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyl diimidazole (60 mg, 0.37 mmol) is added as solid to a solution of the title E compound, N-sulfamoyl-N-[2-(methoxycarbonylmethyl)-phenyl] glycine (112 mg, 0.37 mmol) in THF (5 mL). After 65 h, the solvent is removed by evaporation. The residue is taken up in EtOAc and washed with 1N aqueous HCl followed by brine. The organic solution is dried over anhydrous MgSO4, filtered and concentrated. This residue is then evaporated from diethyl ether to yield [2-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid methyl ester as a white foam: [M−1]−=283.

Workup

  1. customthe solvent is removed by evaporation
  2. washwashed with 1N aqueous HCl
  3. dry with materialThe organic solution is dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis residue is then evaporated from diethyl ether

Sources & evidence

ORD record
ord-0d62f7a2eba9495c8be49064685c6085
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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