Ethylamine → 5-(2,4-Bis-benzyloxy-5-bromophenyl)-isoxazole-3-carboxylic acid ethylamide

HRID 646487Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([Br:17])[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][C:12]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:8][N:7]=1)=O)C.[CH2:34]([NH2:36])[CH3:35]>C(O)C>[CH2:34]([NH:36][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([Br:17])[C:14]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:13][C:12]=2[O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:8][N:7]=1)=[O:3])[CH3:35]

Participants

Conditions

Temperature: 80 °C

Procedure

5-(2,4-bis-benzyloxy-5-bromo-phenyl)-isoxazole-3-carboxylic acid ethyl ester was suspended in ethanol and ethylamine (2M in methanol, 3 eq), the resulting yellow suspension was heated to reflux (80° C.) under nitrogen, at which point the reagents went into solution. This was heated for 14 hours, then left to cool to ambient temperature. A white precipitate formed, which was filtered off and washed with further ethanol before being dried in vacuo.

Workup

temperatureThis was heated for 14 hours
waitleft
temperatureto cool to ambient temperature
customA white precipitate formed
filtrationwhich was filtered off
washwashed with further ethanol
custombefore being dried in vacuo

Sources & evidence

ORD record: ord-964687924e934610adb3849f6cee7be9
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705027B2

Reaction notes

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