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

HRID 1394625Notes

Reaction equation

HRID 1394625 reaction equation
C[O:2][C:3](=[O:42])[CH:4]=[C:5]([C:7]1[N:8]([S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:35])=[O:34])[C:9]2[C:14]([CH:15]=1)=[C:13]([C:16]1[CH:21]=[C:20]([CH:22]([CH3:24])[CH3:23])[CH:19]=[C:18]([CH:25]([CH3:27])[CH3:26])[C:17]=1[O:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:12]=[CH:11][CH:10]=2)[CH3:6].[OH-].[Na+]>CO.O1CCOCC1.Cl.O>[C:36]1([S:33]([N:8]2[C:9]3[C:14](=[C:13]([C:16]4[CH:21]=[C:20]([CH:22]([CH3:23])[CH3:24])[CH:19]=[C:18]([CH:25]([CH3:26])[CH3:27])[C:17]=4[O:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:12]=[CH:11][CH:10]=3)[CH:15]=[C:7]2[C:5]([CH3:6])=[CH:4][C:3]([OH:42])=[O:2])(=[O:34])=[O:35])[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 692207963-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid methyl ester

Product 1

HCID 692199953-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acidYield 107.9%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid methyl ester (74 mg, 0.126 mmol) was dissolved in methanol (1 mL)/dioxane (1 mL) and treated with 1N NaOH (1 mL, 1 mmol) at 60° C. for 2 h. The reaction was diluted with 1N HCl (3 mL)/water (10 mL) and extracted with ethyl acetate (3×10 mL). The organic portions were washed with water (10 mL), brine (10 mL), dried (MgSO4), filtered and evaporated in vacuo to provide 78 mg of a yellow oil. The material was purified using radial chromotagraphy with a gradient of hexane/ethyl acetate to provide 42 mg (58%) of a yellow amorphous foam. 1H NMR (250 MHz, CDCl3): δ 8.08 (d, 1H, 8.2),7.58 (m, 2H), 7.42-7.21 (m, 5H), 7.03 (d, 1H, J=2.2), 6.82 (d, 1H, J=2.2), 6.49 (s, 1H), 6.00 (bs, 1H), 3.28 (sep, 1H, J=6.9), 2.96 (t, 2H, J=6.0), 2.81 (sep, 1H, J=6.9), 1.18 (d 6H, J=6.9), 1.17 (d, 6H, J=6.9). MS [EI+] 574, (M+H)+, [EI−] 572 (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 (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a9b6cf6e502a47c08a47c54f8d731936
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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