Lithium hydroxide, monohydrate → (Z)-3-(Furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoic acid

HRID 2177683Notes

Reaction equation

HRID 2177683 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([O:35][CH3:36])=[C:8]([C:13]([CH2:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3/[CH:26]=[CH:27]\[CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)(=[O:19])=[O:18])=[CH:14][CH:15]=2)[C:9]([O:11]C)=[O:10])=[CH:2]1.O.[OH-].[Li+]>O.O1CCOCC1>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([O:35][CH3:36])=[C:8]([C:13]([CH2:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3/[CH:26]=[CH:27]\[CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)(=[O:19])=[O:18])=[CH:14][CH:15]=2)[C:9]([OH:11])=[O:10])=[CH:2]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69915028(Z)-Methyl 3-(furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoate2×

Product 1

HCID 52913530(Z)-3-(Furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

(Z)-Methyl 3-(furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoate (Intermediate 198, 0.069 g) was added to a solution of lithium hydroxide monohydrate (0.051 g) in water (0.7 ml) and dioxane (3 ml) and the resultant mixture was stirred and heated at 65° C. for 4 days. After cooling, the mixture was diluted with water and washed with diethyl ether. The aqueous layer was acidified with 1M HCl and extracted with ethyl acetate, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by HPLC (C6 phenyl column) eluting with 1:1 methanol:water containing 0.1% formic acid to give (Z)-3-(Furan-3-yl)-2-methoxy-6-((2-(3-(piperidin-1-yl)prop-1-enyl)benzenesulfonyl)methyl)benzoic acid as a white solid.

Workup

  1. temperatureAfter cooling
  2. washwashed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by HPLC (C6 phenyl column)
  9. washeluting with 1:1 methanol

Sources & evidence

ORD record
ord-ae7889dae9944bf8891f8ccc192a293e
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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