Methanol → 5-(2,4-Bis(benzyloxy)-5-chlorophenyl)-N-ethylisoxazole-3-carboxamide
Reaction equation
[CH2:1]([NH2:3])[CH3:2].CO.C([O:8][C:9]([C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[C:20]([Cl:22])[C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][C:17]=2[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:13][N:12]=1)=O)C>C(O)C>[CH2:1]([NH:3][C:9]([C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[C:20]([Cl:22])[C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][C:17]=2[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:13][N:12]=1)=[O:8])[CH3:2]Participants
Conditions
- Temperature
- 80 °C
Procedure
A solution of ethylamine in methanol solution (2.0M; 40 mL; 80 mmol) was added to a stirred suspension of 5-(2,4-bis-benzyloxy-5-chlorophenyl)-isoxazole-3-carboxylic acid ethyl ester (4.40 g; 9.51 mmol) in absolute ethanol (50 ml). The reaction mixture was heated to 80° C. (oil-bath temperature) for five hours. The reaction mixture was allowed to cool to ambient temperature and left to stand overnight. A colourless solid product formed and the reaction mixture was further cooled in an ice-water bath, filtered and washed with cold ethanol (2×20 ml). The colourless product was dried in vacuo to afford 5-(2,4-bis-benzyloxy-5-chlorophenyl)-isoxazole-3-carboxylic acid ethylamide 3.42 g (78%) LCMS: [M+H]+ 465, 463 (37Cl; 35Cl). 1H NMR (400 MHz, CDCl3) δ 1.25 (t, 3H), 3.48 (m, 2H), 5.10 (s, 2H), 5.2 (s, 2H), 6.59 (s, 1H), 6.83 (brt, 1H), 7.08 (s, 1H), 7.30-7.41 (m, 10H), 7.97 (s, 1H).
Workup
- temperatureto cool to ambient temperature
- waitleft
- customA colourless solid product formed
- temperaturethe reaction mixture was further cooled in an ice-water bath
- filtrationfiltered
- washwashed with cold ethanol (2×20 ml)
- customThe colourless product was dried in vacuo
Sources & evidence
- ORD record
- ord-0d74357da15b40818d2eb38e482336cd
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450310B2
Reaction notes
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