Ethyl isobutyrylacetate → HCID 57770808, compound

HRID 2092629Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:8]=[C:9]([N:11]=[N+:12]=[N-:13])[CH:10]=1)=[O:4].[C:21]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])(=O)[CH:22]([CH3:24])[CH3:23].CC[O-].[Na+]>CCO>[CH2:30]([O:29][C:27]([C:26]1[N:13]=[N:12][N:11]([C:9]2[CH:8]=[C:7]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]=2)[C:21]=1[CH:22]([CH3:24])[CH3:23])=[O:28])[CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 5-azido-4′-methyl-biphenyl-3-carboxylic acid methyl ester (200 mg, 0.75 mmol) and ethyl isobutyrylacetate (119 mg, 0.75 mmol) in EtOH (5 mL) was added EtONa (51 mg, 0.75 mmol) and the mixture was heated to 80° C. for two hours, then cooled to room temperature. EtOH was removed from the reaction mixture to afford 5-isopropyl-1-(5-methoxycarbonyl-4′-methyl-biphenyl-3-yl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester as a gel which was used directly in the next step.

Workup

temperaturecooled to room temperature
customEtOH was removed from the reaction mixture

Sources & evidence

ORD record: ord-a6a8ab2414fb45bf820272852eb1bfaa
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440708B2

Reaction notes

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