Hydrochloric Acid → 4-{(3E)-4-{2-[(4-tert-Butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoic acid

HRID 1672689Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 1.1 g (1.97 mmol) of methyl-4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate from Example 102A in 7.20 ml of THF and 3.60 ml of water is mixed with 189 mg (7.89 mmol) of lithium hydroxide and stirred at 60° C. for 12 h. The reaction mixture is adjusted to pH 34 with 1 M hydrochloric acid and concentrated. The residue is taken up on silica gel and purified by chromatography (mobile phase: cyclohexane/ethyl acetate 1:1, with 0.1% formic acid). 990 mg (1.77 mmol, 97% purity, 90% yield) of a solid are isolated.

Workup

concentrationconcentrated
custompurified by chromatography (mobile phase: cyclohexane/ethyl acetate 1:1, with 0.1% formic acid)
custom990 mg (1.77 mmol, 97% purity, 90% yield) of a solid are isolated

Sources & evidence

ORD record: ord-d07bb5265c1747d69737d36b75158eb9
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998988B2

Reaction notes

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