Sodium Hydroxide → 2-((S)-6-((2',6'-dimethyl-4'-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 2280628Notes

Reaction equation

HRID 2280628 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][O:11][CH2:10]2)[CH:5]=[C:4]([CH3:14])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]3[C@H:27]([CH2:30][C:31]([O:33]C)=[O:32])[CH2:28][O:29][C:25]=3[CH:24]=2)[CH:16]=1.[OH-].[Na+]>CO>[CH3:14][C:4]1[CH:5]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][O:11][CH2:10]2)[CH:7]=[C:2]([CH3:1])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]3[C@H:27]([CH2:30][C:31]([OH:33])=[O:32])[CH2:28][O:29][C:25]=3[CH:24]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89701763methyl 2-((S)-6-((2',6'-dimethyl-4'-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 716568142-((S)-6-((2',6'-dimethyl-4'-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-((S)-6-((2′,6′-Dimethyl-4′-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 1d (220 mg, 0.45 mmol) was dissolved in 15 mL of methanol, followed by addition of 3 M aqueous sodium hydroxide solution (1.5 mL, 4.50 mmol). The reaction mixture was reacted for 3 hours. The mixture was concentrated under reduced pressure, mixed with 10 mL of water, and 1M hydrochloric acid was added dropwise to adjust the pH to 2. The resulting solution was 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 to obtain the title compound 2-((S)-6-((2′,6′-dimethyl-4′-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 1 (210 mg, yield 100%) as a white solid.

Workup

  1. customThe reaction mixture was reacted for 3 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionmixed with 10 mL of water, and 1M hydrochloric acid
  4. additionwas added dropwise
  5. extractionThe resulting solution was extracted with ethyl acetate (20 mL×2)
  6. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  7. dry with materialdried with anhydrous magnesium sulphate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e6ded9920d9452da9b1d39d8a055df5
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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