Hydrochloric Acid → 3-[4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid

HRID 1394626Notes

Reaction equation

HRID 1394626 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[C:14]([C:19]4[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[CH:22]=[C:21]([CH:28]([CH3:30])[CH3:29])[C:20]=4[O:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:36]([CH3:41])=[CH:37][C:38]([OH:40])=[O:39])(=O)=O)C=CC=CC=1.[OH-].[K+].Cl>C(O)C.O1CCOCC1>[CH2:32]([O:31][C:20]1[C:21]([CH:28]([CH3:30])[CH3:29])=[CH:22][C:23]([CH:25]([CH3:26])[CH3:27])=[CH:24][C:19]=1[C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[CH:12]=[C:11]([C:36]([CH3:41])=[CH:37][C:38]([OH:40])=[O:39])[NH:10]2)[CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 692199953-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid

Product 1

HCID 668993213-[4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acidYield 103%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

3-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid (32 mg, 0.056 mmol) was dissolved in ethanol (1 mL)/dioxane (1 mL) and treated with 2.5N KOH (1 mL, 1 mmol) at 70-75° C. for 24 h. The reaction was neutralized with 1N HCl and extracted with ethyl acetate (3×10 mL). The organic portions were washed with water (10 mL), brine (10 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 25 mg of a residue. The material was purified using radial chromatography with a gradient of hexane/ethyl acetate to provide 13 mg (53%) of a yellow amorphous foam. 1H NMR (250 MHz, CDCl3): δ 8.26 (bs, 1H), 7.26-7.15 (m, 3H), 7.06 (m, 2H), 6.83 (s, 1H), 6.11 (s, 1H), 3.37 (m, 1H), 3.22 (t, 2H, J=6.3), 2.86 (m, 1H), 2.55 (s, 3H), 1.23 (m, 14H), 0.95 (m, 2H), 0.54 (t, 3H, J=7.2). MS [EI+] 434, (M+H)+, [EI−] 432 (M−H)+.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe organic portions were washed with water (10 mL), brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8aff45aeb5804f2981a22829f2e0f943
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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