Potassium Hydroxide → HCID 10410832, compound

HRID 2212159Notes

Reaction equation

HRID 2212159 reaction equation
C(O[CH2:5][C:6]1[N:7]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=2)[C:8]2[C:13]([C:14]=1[C:15](=[O:19])[C:16]([OH:18])=[O:17])=[CH:12][C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1)=[CH:10][CH:9]=2)(=O)C.[OH-].[K+]>C1COCC1.CO>[C:34]([C:31]1[CH:30]=[CH:29][C:28]([CH2:27][N:7]2[C:8]3[C:13](=[CH:12][C:11]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=4)=[CH:10][CH:9]=3)[C:14]3[C:15](=[O:19])[C:16](=[O:18])[O:17][CH2:5][C:6]2=3)=[CH:33][CH:32]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21964290HCID 21964290, compound

Product 1

HCID 10410832HCID 10410832, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of [2-[(acetyloxy)methyl]-1-(4-tert-butylbenzyl)-5-(3-methylphenyl)-1H-indol-3-yl](oxo)acetic acid (0.27 g, 0.63 mmol) and aqueous potassium hydroxide (1.0 N, 1.1 mL, 1.1 mmol) in THF:MeOH (1:1, 6.6 mL) was stirred at room temperature for 4 h. The reaction mixture was evaporated to dryness. The residue was washed with water and hexane to give an oil. This oil was partitioned between methylene chloride (80 mL) and 15% aqueous HCl (15 mL) with stirring. The organic layer was separated, washed with water and evaporated to afford the title compound as an off-white solid, mp: 196–197° C. Mass spectrum (ESI, [M+H]+) m/z 438. 1HNMR (400 MHz, DMSO-d6): δ 8.21 (s, 1H), 7.75 (d, 2H, J=8.55 Hz), 7.66 (dd, 1H, J=8.70 and 1.52 Hz), 7.50 (s, 1H), 7.47 (d, 1H, J=8.71 Hz), 7.38–7.35 (m, 3H), 7.20–7.17 (m, 3H), 5.92 (s, 2H), 5.50 (s, 2H), and 2.39 ppm (s, 3H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. washThe residue was washed with water and hexane
  3. customto give an oil
  4. customThis oil was partitioned between methylene chloride (80 mL) and 15% aqueous HCl (15 mL)
  5. customThe organic layer was separated
  6. washwashed with water
  7. customevaporated

Sources & evidence

ORD record
ord-eee946ad22324c20a4713f7f07fab9bb
Source dataset
uspto-grants-2006_09
Patent number
US07101903B2

Reaction notes

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