Potassium Hydroxide → 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylic acid

HRID 1713945Notes

Reaction equation

HRID 1713945 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18]C)=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:8]=2[C:26]2[O:30][CH:29]=[N:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CO.C1COCC1.O.CCOC(C)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:8]=2[C:26]2[O:30][CH:29]=[N:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68437594methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylate

Product 1

HCID 114635753-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylate (from Step 5) in MeOH/THF/H2O (0.05 M, 1:1:1, v:v:v) was added KOH (5 eq.). The resulting solution was stirred at RT overnight. The reaction mixture was diluted with EtOAc, then washed with hydrochloric acid (1N), brine, and dried over Na2SO4. Evaporation gave an off-white foam, which was purified by RP-HPLC (column: Waters X-terra C18, 19×150 mm, 5 micron; flow 20 mL/min) to give the title compound as a white powder after lyophilization (53%).

Workup

  1. washwashed with hydrochloric acid (1N), brine
  2. dry with materialdried over Na2SO4
  3. customEvaporation
  4. customgave an off-white foam, which
  5. customwas purified by RP-HPLC (column: Waters X-terra C18, 19×150 mm, 5 micron; flow 20 mL/min)

Sources & evidence

ORD record
ord-5488244d0d874fe68b68748858dc9334
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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