Trifluoroacetic acid → HCID 21935915, compound

HRID 1242479Notes

Reaction equation

C([O:5][C:6](=[O:39])[C:7]([CH3:38])([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](=[O:37])[NH:18][CH2:19][C:20]2[C:21]([CH3:36])=[N:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)=[CH:12][CH:11]=1)[CH3:8])(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:38][C:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](=[O:37])[NH:18][CH2:19][C:20]2[C:21]([CH3:36])=[N:22][C:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=3)=[CH:24][CH:25]=2)=[CH:12][CH:11]=1)([CH3:8])[C:6]([OH:39])=[O:5]

Participants

Conditions

Temperature: 50 °C

Procedure

0.23 g (0.42 mmol) of 2-methyl-2-[4-({[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-carbamoyl}-methyl)-phenoxy]-propionic acid tert-butyl ester was dissolved in 10 ml of MeCl2. Then, 0.14 ml=0.139 g (1.28 mmol) of anisole was added followed by 0.32 ml=0.48 g (4.2 mmol) of trifluoroacetic acid. The reaction mixture was stirred at reflux (oil bath 50° C.) for 16 hours. It was then poured into crashed ice and extracted twice with MeCl2. The combined organic phases were washed with water, dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by flash chromatography (SiO2, MeCl2/MeOH) to give 0.17 g of the title compound as colorless solid.

Workup

additionIt was then poured
extractionextracted twice with MeCl2
washThe combined organic phases were washed with water
dry with materialdried over anhydrous magnesium sulfate
customevaporated
customThe crude product was purified by flash chromatography (SiO2, MeCl2/MeOH)

Sources & evidence

ORD record: ord-876e87ecf6e6445b958e45fae8cf5230
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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