Potassium Hydroxide → HCID 67019966, compound

HRID 1673211Notes

Reaction equation

HRID 1673211 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([CH2:26][C:27]([O:29]CC)=[O:28])[CH2:24][C:23]([CH3:33])([CH3:32])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[OH-].[K+]>C1COCC1.CO.O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([CH2:26][C:27]([OH:29])=[O:28])[CH2:24][C:23]([CH3:33])([CH3:32])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 14797Potassium HydroxideHCID 24992107HCID 24992107, compound

Product 1

HCID 67019966HCID 67019966, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To the product of Example 76 (46.5 mg, 0.127 mmol) was added KOH (10.3 mg, 0.184 mmol) in THF (1.5 mL), MeOH (0.2 mL) and water (0.075 mL). The reaction was heated to 50° C. After 27 min the reaction was cooled and diluted with EtOAc. The solution was washed with aq 2 M HCl and brine, dried (Na2SO4), filtered and concentrated to afford the product that was not purified further (LC-2) HPLC/MS: 476.0 (M+1), 478.0 (M+3); Rt=3.96 min.

Workup

  1. temperatureAfter 27 min the reaction was cooled
  2. washThe solution was washed with aq 2 M HCl and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford the product that
  7. customwas not purified further (LC-2) HPLC/MS

Sources & evidence

ORD record
ord-5ea1a6b16d0a4577a996e0dd934e5c85
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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