Lithium Hydroxide → (4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid

HRID 524387Notes

Reaction equation

HRID 524387 reaction equation
C([O:3][C:4](=[O:25])[CH:5]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:22]2[CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)[O:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)C.[Li+].[OH-]>O1CCCC1>[CH:22]1([S:19]([C:16]2[CH:15]=[CH:14][C:13]([CH:5]([O:6][CH:7]3[CH2:8][CH2:9][O:10][CH2:11][CH2:12]3)[C:4]([OH:25])=[O:3])=[CH:18][CH:17]=2)(=[O:21])=[O:20])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59610050(4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid ethyl ester

Product 1

HCID 59610020(4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of intermediate 2-[4-(Cyclopropanesulfonyl)phenyl]-2-(tetrahydro-pyran-4-yloxy)acetic acid ethyl ester (8.0 g, 21 mmol) in tetrahydrofuran (80 mL) was added a solution of LiOH (2.27 g in 40 mL of water, 54 mmol) at 25° C. and stirred for 2 h. Completion of reaction was confirmed by TLC. Organic solvent was removed under reduced pressure. The aqueous layer was acidified to pH 2-3 using 1 N HCl. White solid obtained was filtered through Buchner funnel dried under vacuum to afford pure product.

Workup

  1. customCompletion of reaction
  2. customOrganic solvent was removed under reduced pressure
  3. customWhite solid obtained
  4. filtrationwas filtered through Buchner funnel
  5. customdried under vacuum
  6. customto afford pure product

Sources & evidence

ORD record
ord-bab3978e283d4bcd975cf6ca9fbc2d23
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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