Sodium Hydroxide → HCID 66900102, compound

HRID 1394622Notes

Reaction equation

HRID 1394622 reaction equation
C[O:2][C:3](=[O:44])[CH:4]=[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12](S(C1C=CC=CC=1)(=O)=O)[CH:11]=[C:10]2[C:25]1[CH:30]=[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:28]=[C:27]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:26]=1[O:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH3:6].[OH-].[Na+]>CO.O1CCOCC1.Cl>[CH2:40]([O:39][C:26]1[C:27]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:28][C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:30][C:25]=1[C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:5]([CH3:6])=[CH:4][C:3]([OH:44])=[O:2])[CH:8]=2)[NH:12][CH:11]=1)[CH2:41][CH2:42][CH3:43]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 69218357HCID 69218357, compound

Product 1

HCID 66900102HCID 66900102, compoundYield 115.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

3-[1-Benzenesulfonyl-3-(2-butoxy-3,5-di-tert-butyl-phenyl)-1H-indol-5-yl]-but-2-enoic acid methyl ester (187 mg, 0.3 mmol) was dissolved in methanol (2 mL)/dioxane (3.5 mL) and treated with 1N NaOH (2 mL) at 60° C. for 4 h. Diluted with 1N HCl (3 mL) and extracted with ethyl acetate (3×10 mL). The combined organic portions were washed with water (10 mL), brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo to provide 160 mg of an orange solid. The material was purified using radial chromatography (eluet: hexane/ethyl acetate gradient) to provide 85 mg (62%) of a yellow foam. 1H NMR (250 MHz, CDCl3): δ 8.24 (bs, 1H), 7.88 (s, 1H), 7.40-7.35 (m, 3H), 7.28 (d, 2H), 6.18 (s, 1H), 3.37 (t, 2H, J=6.5), 2.61 (s, 3H), 1.41 (s, 9H), 1.28 (s, 9H), 1.19-0.98 (m, 4H), 0.56 (t, 3H, J=7.2). MS [EI+] 462 M+H)+, [EI−] 460 (M−H)+. Anal. Calcd for C30H39NO3: C, 78.05; H, 8.52; N, 3.03. Found: C, 78.10; H, 8.30; N, 3.02.

Workup

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

Sources & evidence

ORD record
ord-e090f37f6d354298b7f4f900589f4baf
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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