Potassium Hydroxide → HCID 10179618, compound

HRID 2086158Notes

Reaction equation

HRID 2086158 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH3:15])[C:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([C:24](=[O:31])[N:25]([CH:27]3[CH2:30][CH2:29][CH2:28]3)[CH3:26])[CH:18]=1)=[C:10]([CH3:32])[CH:9]=2)=[O:5])C.[OH-].[K+]>CO.O>[CH:27]1([N:25]([CH3:26])[C:24]([C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=2[OH:23])[O:16][C:11]2[C:12]([CH3:15])=[C:13]3[C:8](=[CH:9][C:10]=2[CH3:32])[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]3)=[O:31])[CH2:28][CH2:29][CH2:30]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12150670HCID 12150670, compound

Product 1

HCID 10179618HCID 10179618, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-[3-(Cyclobutyl-methyl-carbamoyl)-4-hydroxy-phenoxy]-4,6-dimethyl-1H-indole-2-carboxylic acid ethyl ester (102 mg, 0.23 mmol) in methanol (2 mL) at room temperature was added 3N potassium hydroxide (0.44 mL) and the mixture was stirred at room temperature for 7 hours. The reaction mixture was diluted with water (10 mL) and washed with EtOAc/Et2O (1/1, 3 times 5 mL). The aqueous solution was acidified with hydrochloric acid and then extracted with ethyl acetate (3 times 5 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to afford the title compound (81 mg) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ11.08 (s, 1H), 7.15-7.14 (d, 2H), 6.76 (s+m, 2H), 6.33 (br s, 1H), 4.25-4.16 (m, 1H), 2.90 (s, 3H), 2.25 (s, 3H), 2.22-2.19 (m, 2H), 2.15 (s, 3H), 1.95-1.85 (m, 2H), 1.60-1.48 (m, 2H). MS (APCI+) Calc: 408.2, Found: 409.2 (M+1).

Workup

  1. washwashed with EtOAc/Et2O (1/1, 3 times 5 mL)
  2. extractionextracted with ethyl acetate (3 times 5 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a0678e45c0644eb4a09ef3e4e9409908
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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