Lithium Hydroxide → (+/-)-3-(4-Ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoic Acid

HRID 2099755Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]([CH2:16][C:17]2[CH:25]=[C:24]([CH3:26])[C:23]3[C:19](=[CH:20][N:21]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:22]=3)[CH:18]=2)[CH2:10][C:11]([O:13]CC)=[O:12])[CH:4]=1)[CH3:2].[OH-].[Li+]>O1CCCC1>[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]([CH2:16][C:17]2[CH:25]=[C:24]([CH3:26])[C:23]3[C:19](=[CH:20][N:21]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[N:22]=3)[CH:18]=2)[CH2:10][C:11]([OH:13])=[O:12])[CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a flask containing (±)-ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate (80 mg, 0.166 mmol, 1.0 equiv) in tetrahydrofuran (4 mL) was added lithium hydroxide (2.0 M, 0.34 mL, 4.0 equiv). The suspension was heated at 60° C. under nitrogen overnight. The reaction mixture was concentrated in vacuo. Hydrochloric acid (1 N, 0.6 mL) was added and the solution was extracted with ethyl acetate. The aqueous solution was adjusted to pH 7 with sodium hydroxide (1 N) and re-extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to give a light yellow oil. MS (ESI) 454 (MH)+.

Workup

concentrationThe reaction mixture was concentrated in vacuo
additionHydrochloric acid (1 N, 0.6 mL) was added
extractionthe solution was extracted with ethyl acetate
extractionre-extracted with ethyl acetate
washThe combined ethyl acetate layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customto give a light yellow oil

Sources & evidence

ORD record: ord-744c724ff79648e6b2ec58ce1045cd6a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569578B2

Reaction notes

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