Water → HCID 68517352, compound

HRID 1717380Notes

Reaction equation

O=[C:2]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][C:4]([O:6]CC)=[O:5].[N:14]([C:17]1[CH:27]=[CH:26][C:20]([C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1)=[N+:15]=[N-:16].[O-]CC.[Na+].O>C(O)C>[CH2:24]([NH:23][C:21]([C:20]1[CH:26]=[CH:27][C:17]([N:14]2[C:2]([C:9]3[S:10][CH:11]=[CH:12][CH:13]=3)=[C:3]([C:4]([OH:6])=[O:5])[N:16]=[N:15]2)=[CH:18][CH:19]=1)=[O:22])[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 3-oxo-3-(2-thienyl)propanoate (500 mg, 2.50 mmol) and 4-azido-N-ethylbenzamide (500 mg, 2.50 mmol, 1.0 eq.) obtained in Example 43a) were dissolved in ethanol (20 ml), a solution of sodium ethoxide in ethanol (20%, 1.3 g, 3.82 mmol, 1.5 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 60° C. for 7 hr. Water (20 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was diluted with 2% aqueous sodium carbonate solution (20 ml) and washed with ethyl acetate-hexane (2:1). The organic layer was extracted with 2% aqueous sodium carbonate solution. The aqueous layers were combined, acidified (pH<3) with 6N hydrochloric acid and stood still at 0° C. The precipitate was collected by filtration, washed with ice-cold water and dried to give the title compound as a pale-yellow powder (764 mg, 89%).

Workup

customwas evaporated
additionthe residue was diluted with 2% aqueous sodium carbonate solution (20 ml)
washwashed with ethyl acetate-hexane (2:1)
extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution
customstood still at 0° C
filtrationThe precipitate was collected by filtration
washwashed with ice-cold water
customdried

Sources & evidence

ORD record: ord-3c83e216b78e460fa9b524def98dda90
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803822B2

Reaction notes

Loading…