Triethylamine → (4'-{3-Methyl-4-[1-(2-trifluoromethyl-phenyl)-ethoxycarbonylamino]-isoxazol-5-yl}-biphenyl-4-yl)-acetic acid ethyl ester

HRID 553665Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:23][N:22]=[C:21]([CH3:24])[C:20]=3C(O)=O)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].[CH3:28][CH:29]([OH:40])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]([F:39])([F:38])[F:37].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:48])C=CC=CC=1.C([N:60]([CH2:63]C)CC)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[O:23][N:22]=[C:21]([CH3:24])[C:20]=3[NH:60][C:63]([O:40][CH:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:37])([F:38])[F:39])[CH3:28])=[O:48])=[CH:17][CH:18]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

5-(4′-Ethoxycarbonylmethyl-biphenyl-4-yl)-3-methyl-isoxazole-4-carboxylic acid (0.150 g, 0.41 mmol), alpha-methyl-2-trifluoromethylbenzyl alcohol (0.094 g, 0.49 mmol), diphenylphosphoryl azide (0.11 mL, 0.49 mmol), and triethylamine (0.11 mL, 0.49 mmol) were combined in toluene (3 mL) and stirred at 80° C. for 2 hours. After cooling, the mixture was worked-up to give the title compound.

Workup

temperatureAfter cooling

Sources & evidence

ORD record: ord-6141fd1f436d4738908751339b5c3784
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048902B2

Reaction notes

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