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Lithium Hydroxide → (S)-2-(6-((4'-((1-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 2280665
Notes
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Reaction equation

HRID 2280665 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:9][CH:8]([O:10][C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]5[CH:39]=[CH:38][C:29]6[C@H:30]([CH2:33][C:34]([O:36]C)=[O:35])[CH2:31][O:32][C:28]=6[CH:27]=5)[CH:19]=4)=[C:13]([CH3:40])[CH:12]=3)[CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[OH-].[Li+]>CO>[CH:1]1([C:4]([N:6]2[CH2:9][CH:8]([O:10][C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]5[CH:39]=[CH:38][C:29]6[C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][O:32][C:28]=6[CH:27]=5)[CH:19]=4)=[C:13]([CH3:40])[CH:12]=3)[CH2:7]2)=[O:5])[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117699344(S)-methyl 2-(6-((4'-((1-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 71657093(S)-2-(6-((4'-((1-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acidYield 44%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

The crude (S)-methyl 2-(6-((4′-((1-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 15b (46 mg, 0.09 mmol) was dissolved in 3 mL of methanol, followed by addition of 1M aqueous lithium hydroxide solution (0.5 mL, 0.50 mmol). The reaction solution was stirred for 3 hours. The resulting solution was concentrated under reduced pressure, 1M hydrochloric acid was added dropwise to adjust the pH to 3, 3 mL of water were added, and then the 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 (S)-2-(6-((4′-((1-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 15 (20 mg, yield 44.0%) as a yellow solid.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure, 1M hydrochloric acid
  2. additionwas added dropwise
  3. additionwere added
  4. extractionthe solution was extracted 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

Sources & evidence

ORD record
ord-f17bf3614d1a4dd893b3ef64a2b1382b
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139548B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes