Benzyl bromoacetate → HCID 20557555, compound

HRID 1660129Notes

Reaction equation

HRID 1660129 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[N:5]2[C:4](=[O:15])[NH:3]1.CC(C)([O-])C.[K+].Br[CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(O)(C)(C)C>[CH3:14][O:13][C:11]([CH:10]1[CH2:9][CH2:8][CH2:7][N:6]2[C:2](=[O:1])[N:3]([CH2:23][C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[C:4](=[O:15])[N:5]12)=[O:12]

Participants

5

Reactant 3

HCID 62576Benzyl bromoacetateHCID 20557501HCID 20557501, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20557555HCID 20557555, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

1.50 g (0.007 mol) of methyl hexahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-5-carboxylate were dissolved in 40 ml of dry tert.butanol. A solution of 0.87 g (0.008 mol) of potassium tert.butoxide in 50 ml of dry tert.butanol was added and the mixture was stirred under reflux and under a nitrogen atmosphere for 4 hours. 1.61 g (0.007 mol) of benzyl bromoacetate were added and the heating was continued for a further 4 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was chromatographed on silica gel using chloroform for the elution to give 1.32 g (52%) of benzyl 5-methoxycarbonyl-2,3,5,6,7,8-hexahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-2-acetate of melting point 103°-106° C. (from dichloromethane/hexane).

Workup

  1. temperatureunder reflux and under a nitrogen atmosphere for 4 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-cfef32a872624689b3b5b231855fef83
Source dataset
uspto-grants-1981_12
Patent number
US04307094

Reaction notes

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