Sodium Hydroxide → HCID 66900003, compound

HRID 1394658Notes

Reaction equation

HRID 1394658 reaction equation
C[O:2][C:3](=[O:43])[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][CH3:42])[CH3:6].[OH-].[Na+]>CO.O1CCOCC1.Cl>[C:35]([C:27]1[C:26]([O:39][CH2:40][CH2:41][CH3:42])=[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:43])=[O:2])[CH:8]=3)[NH:12][CH:11]=2)[CH:30]=[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:28]=1)([CH3:36])([CH3:37])[CH3:38]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 69220364HCID 69220364, compound

Product 1

HCID 66900003HCID 66900003, compoundYield 127.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

3-[1-Benzenesulfonyl-3-(3,5-di-tert-butyl-2-propoxy-phenyl)-1H-indol-5-yl]-but-2-enoic acid methyl ester (171 mg, 0.28 mmol) was dissolved in methanol (1.5 mL)/dioxane (3 mL) and treated with 1N NaOH (2 mL) at 60° C. for 4 h. The reaction was diluted with 1N HCl (10 mL) and extracted with ethyl acetate (3×15 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 a brown solid. The material was purified using radial chromatography (eluent:hexane/ethyl acetate gradient) to provide 73 mg (58%) of a yellow foam. Mp. 105-115° C. 1H NMR (250 MHz, CDCl3): δ 8.31 (bs, 1H), 7.98 (bs, 1H, 8.7), 7.92 (m, 2H) 7.70 (m, 21), 7.47-7.35 (m, 5H), 6.27 (bs, 1H), 3.42 (t, 2H, J=6.4) 2.68 (d, 3H, J=1.0), 1.49 (s, 9H), 1.37 (s, 9H), 1.32 (m, 2H) 0.68 (t, 3H, J=7.4). MS [EI+] 448 (M+E)+, [EI−] 446 (M−H)+. Analytical (C29H37NO3): Calculated C, 77.81; H, 8.33; N, 3.13. Found: C, 77.89; H, 8.68; N, 2.94.

Workup

  1. extractionextracted with ethyl acetate (3×15 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-8dda12028ba04a049846f33e9247879f
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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