Methanol → 5-(2,4-Bis(benzyloxy)-5-chlorophenyl)-N-ethylisoxazole-3-carboxamide

HRID 389927Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Ethylamine in MeOH solution (2 M, 80 mmol, 40 ml) was added to a suspension of ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate (9.51 mmol) in EtOH (50 ml) and the reaction mixture was heated to 80° C. with stirring for 18 h, affording a yellow homogeneous solution, which was allowed to cool to RT. A flocculent colourless solid formed upon cooling to 4° C. After filtration, washing with cold EtOH and drying under vacuo, the desired compound was obtained.

Workup

customaffording a yellow homogeneous solution, which
temperatureto cool to RT
customA flocculent colourless solid formed
temperatureupon cooling to 4° C
filtrationAfter filtration
washwashing with cold EtOH
customdrying under vacuo

Sources & evidence

ORD record: ord-0bb2692d6c91456d98a7eb896fca0e00
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383616B2

Reaction notes

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