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

HRID 548569Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (4-{3-[3-(4-methanesulfonyl-phenylethynyl)-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester (50 mg, 0.08 mmol) in THF (1.25 ml) and methanol (0.25 ml) was added a ice-cold solution of LiOH (1 M, 1.25 ml). The reaction mixture was stirred at 0° C. for 460 min., after which water (10 ml) and aqueous HCl (1M, 1.75 ml) were added. The mixture was extracted with ethyl acetate (2×10 ml), and the combined organic phases were dried and evaporated to give the title compound in 15 mg (31%) yield.

Workup

extractionThe mixture was extracted with ethyl acetate (2×10 ml)
customthe combined organic phases were dried
customevaporated

Sources & evidence

ORD record: ord-3bae62b6c69c4441ad55f04eee84df8b
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943612B2

Reaction notes

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