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

HRID 2097273Notes

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-76100f2209f14ac9888c8911b97d23d4
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450310B2

Reaction notes

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