Lithium Hydroxide → HCID 89701780, compound

HRID 2280658Notes

Reaction equation

HRID 2280658 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:23]=[CH:22][C:13]3[C@H:14]([CH2:17][C:18]([O:20]C)=[O:19])[CH2:15][O:16][C:12]=3[CH:11]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:24]1[C:29]([CH3:30])=[CH:28][C:27]([O:31][C@H:32]2[CH2:36][CH2:35][O:34][CH2:33]2)=[CH:26][C:25]=1[CH3:37].[OH-].[Li+]>O1CCCC1.CO>[CH3:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:23]=[CH:22][C:13]3[C@H:14]([CH2:17][C:18]([OH:20])=[O:19])[CH2:15][O:16][C:12]=3[CH:11]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:24]1[C:25]([CH3:37])=[CH:26][C:27]([O:31][C@H:32]2[CH2:36][CH2:35][O:34][CH2:33]2)=[CH:28][C:29]=1[CH3:30]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89701783methyl 2-((S)-6-((2,2',6'-trimethyl-4'-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 89701780HCID 89701780, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-((S)-6-((2,2′,6′-trimethyl-4′-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 12f (100 mg, 0.20 mmol) was dissolved in 4 mL of a mixture of the solvents tetrahydrofuran and methanol (V/V=1:1), followed by addition of 2M aqueous lithium hydroxide solution (1 mL, 2 mmol). The reaction solution was stirred for 2 hours. The resulting solution was concentrated under reduced pressure. The residue was mixed with 10 mL of water, 1M hydrochloric acid was added dropwise to adjust the pH to 1˜2 and extracted with ethyl acetate (20 mL×2). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purifed using a method of preparative separation to obtain the title compound 2-((S)-6-((2,2′,6′-trimethyl-4′-(((S)— tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 12 (80 mg, yield 83.0%) as a white solid.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. additionThe residue was mixed with 10 mL of water, 1M hydrochloric acid
  3. additionwas added dropwise
  4. extractionextracted with ethyl acetate (20 mL×2)
  5. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  6. dry with materialdried with anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customa method of preparative separation

Sources & evidence

ORD record
ord-2841077b7f11404fb2832842733998e3
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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