Hydrochloric Acid → (2-Methyl-4-{3-[3-(3-morpholin-4-yl-prop-1-ynyl)-5-(4-trifluoromethyl-phenylethynyl)-phenyl]-prop-2-ynyloxy}-phenoxy)-acetic acid

HRID 548563Notes

Reaction equation

C[O:2][C:3](=[O:44])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]#[C:15][C:16]2[CH:21]=[C:20]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[CH:19]=[C:18]([C:34]#[C:35][CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH:17]=2)=[CH:8][C:7]=1[CH3:43].[Li+].[OH-].O.Cl>C1COCC1.CO>[CH3:43][C:7]1[CH:8]=[C:9]([O:12][CH2:13][C:14]#[C:15][C:16]2[CH:21]=[C:20]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[CH:19]=[C:18]([C:34]#[C:35][CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH:17]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([OH:44])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2-methyl-4-{3-[3-(3-morpholin-4-yl-prop-1-ynyl)-5-(4-trifluoromethylphenylethynyl)-phenyl]-prop-2-ynyloxy}-phenoxy)-acetic acid methyl ester (0.26 g, 0.51 mmol) in THF (5.3 ml) and methanol (1 ml) was added a ice-cold solution of LiOH (1 M, 5.3 ml). The reaction mixture was stirred at 0° C. for 45 min., after which water (10 ml) and aqueous HCl (1M, 7.4 ml) were added. The mixture was extracted with ethyl acetate (2×80 ml), and the combined organic phases were dried and evaporated to give the title compound in 272 mg (94%) yield.

Workup

extractionThe mixture was extracted with ethyl acetate (2×80 ml)
customthe combined organic phases were dried
customevaporated

Sources & evidence

ORD record: ord-9d0fb07c27384535a4002ba4d0b13ea4
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943612B2

Reaction notes

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