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

HRID 2099755
Notes
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Reaction equation

HRID 2099755 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57794570(+/-)-Ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate

Product 1

HCID 57794674(+/-)-3-(4-Ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionHydrochloric acid (1 N, 0.6 mL) was added
  3. extractionthe solution was extracted with ethyl acetate
  4. extractionre-extracted with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes