Hydrochloric Acid → HCID 86668761, compound

HRID 533527

Reaction equation

HRID 533527 reaction equation
[OH-].[Li+].[Br:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([CH3:22])([S:18]([CH3:21])(=[O:20])=[O:19])[C:13]([O:15]CC)=[O:14])=[CH:6][CH:5]=1.O1CCCC1CO.O.Cl>O>[Br:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([CH3:22])([S:18]([CH3:21])(=[O:20])=[O:19])[C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66577907Tetrahydrofuran-methanol waterHCID 86668759Ethyl 4-(6-bromopyridin-3-yl)-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 86668761HCID 86668761, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of lithium hydroxide (357 mg, 8.5 mmol, 4.0 equiv) and ethyl 4-(6-bromopyridin-3-yl)-2-methyl-2-(methylsulfonyl)butanoate (775 mg, 2.1 mmol, 1.0 equiv) in 1:1:1 tetrahydrofuran-methanol-water (3 mL) was allowed to stir at room temperature for 2 h. The reaction was diluted with water (150 mL), acidified (to pH=2) with 0.5 M hydrochloric acid, and then was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide the title compound (716 mg, 98%). MS (LCMS) m/z 334.1 (M−1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.56 (s, 3H) 2.03 (td, J=12.78, 5.27 Hz, 1H) 2.31 (td, J=12.68, 4.68 Hz, 1H) 2.51 (td, J=12.98, 4.49 Hz, 1H) 2.59-2.70 (m, 1H) 2.96 (s, 3H) 7.30-7.39 (m, 2H) 8.07 (d, J=1.56 Hz, 1H).

Workup

  1. extractionwas extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cf975d366cf4e32b5a686ddc850d8c2
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Linked notes

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