Sodium Hydroxide → HCID 66899666, compound

HRID 1394663Notes

Reaction equation

HRID 1394663 reaction equation
C[O:2][C:3](=[O:45])[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][C:41]([F:44])([F:43])[F:42])[CH3:6].[OH-].[Na+]>CO.O1CCOCC1.Cl>[C:35]([C:27]1[C:26]([O:39][CH2:40][C:41]([F:44])([F:42])[F:43])=[C:25]([C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:5]([CH3:6])=[CH:4][C:3]([OH:45])=[O:2])[CH:8]=3)[NH:12][CH:11]=2)[CH:30]=[C:29]([C:31]([CH3:33])([CH3:34])[CH3:32])[CH:28]=1)([CH3:36])([CH3:37])[CH3:38]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 69218898HCID 69218898, compound

Product 1

HCID 66899666HCID 66899666, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

3-{1-Benzenesulfonyl-3-[3,5-di-tert-butyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-1H-indol-5-yl}-but-2-enoic acid methyl ester was dissolved in methanol (1.5 mL)/dioxane (3 mL) and treated with 1N NaOH (2.0 mL) at 60° C. for 2.5 h. Diluted with 1N HCl (15 mL) and extracted with ethyl acetate (3×15 mL). The combined organic portions were washed with water (30 mL), brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo to provide 145 mg of crude material. The material was purified using radial chromatography by (eluet: hexane/ethyl acetate gradient) to provide 72 mg (53%) of a pale yellow solid. Mp. 146-153° C. 1H NMR (250 MHz, CDCl3): δ 8.43 (bs, 1H), 7.95 (s, 1H), 7.53 (d, 1H, J=2.4), 7.46 (m, 3H), 7.38 (d, 1H, J=2.5), 6.26 (d, 1H, J=1.1), 3.86 (q, 2H, J=8.6), 2.69 (d, 3H, J=1.0), 1.49 (s, 9H), 1.37 (s, 9H). MS [EI+] 488 (M+H)+, [EI−] 486 (M−H)+. Analytical (C29H37NO3): Calculated C, 68.98; H, 6.62; N, 2.87. Found: C, 66.45; H, 6.85; N, 2.59.

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washThe combined organic portions were washed with water (30 mL), brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide 145 mg of crude material
  7. customThe material was purified

Sources & evidence

ORD record
ord-ae27a5150d2b459c84259bde60d83915
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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