Hydrochloric Acid → (4-{[{4-[(4-Butylphenyl)ethynyl]benzyl}(ethylsulfonyl)amino]-methyl}phenoxy)acetic acid

HRID 551916Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl (4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(ethylsulfonyl)amino]-methyl}phenoxy)acetate (7 mg, 0.013 mmol) in EtOH (1 mL) was added an aqueous solution of NaOH (20 μL, 5N). The reaction mixture was stirred at 70° C. for 2 hrs. Then an aqueous solution of HCl (1N) was added and extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4 and the solvents were removed under reduced pressure to give 6 mg (90%) of the title compound as a pale yellow oil. HPLC, Rt: 5.0 min (purity: 75.0%). LC/MS, M+(ESI): 520.5, M−(ESI): 518.3.

Workup

extractionextracted with EtOAc (2×)
dry with materialThe combined organic layers were dried over Na2SO4
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-a878b99e8ca54aae8a21905140c2ed10
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

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