Sodium Hydroxide → HCID 66898958, compound

HRID 1394620Notes

Reaction equation

HRID 1394620 reaction equation
C[O:2][C:3](=[O:31])[CH:4]=[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[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][CH3:30])[CH3:6].[OH-].[Na+]>CO.O1CCOCC1.Cl.O>[CH2:29]([O:28][C:17]1[C:18]([CH:25]([CH3:27])[CH3:26])=[CH:19][C:20]([CH:22]([CH3:23])[CH3:24])=[CH:21][C:16]=1[C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:5]([CH3:6])=[CH:4][C:3]([OH:31])=[O:2])[CH:8]=2)[NH:12][CH:11]=1)[CH3:30]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 69217857HCID 69217857, compound

Product 1

HCID 66898958HCID 66898958, compoundYield 62%

Reagents, catalysts & solvents 4

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

Procedure

3-[3-(2-Ethoxy-3,5-diisopropyl-phenyl)-1H-indol-5-yl]-but-2-enoic acid methyl ester (77 mg, 0.14 mmol) was dissolved in methanol (1 mL)/dioxane (1 mL) and treated with 1N NaOH (1 mL) at 55° C. for 5 h. Diluted with 1N HCl (3 mL)/water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic portions were washed with brine (2×10 mL), dried (MgSO4), filtered and concentrated in vacuo to provide 68 mg. The material was purified by radial chromatography using a hexane/ethyl acetate gradient to provide 34 mg (62%) of a yellow foam. 1H NMR (250 MHz, CDCl3): δ 8.33 (bs, 1H), 8.04 (s, 1H), 7.58 (d, 1H, J=2.4), 7.44 (s, 1H), 7.29 (d, 1H, J=2.2), 7.09 (d, 1H, J=2.2), 6.27 (s, 1H), 3.56-3.38 (m, 3H), 2.95 (sep, 1H, J=6.9), 2.70 (s, 3H), 1.32 (s, 12H, J=6.9), 1.08 (t, 3H, J=7.0). MS [EI−] 404 (M−H)+.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic portions were washed with brine (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide 68 mg
  7. customThe material was purified by radial chromatography

Sources & evidence

ORD record
ord-491704c5c9d14a86bf807b792e773225
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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