Potassium Hydroxide → HCID 59423907, compound

HRID 2387690Notes

Reaction equation

HRID 2387690 reaction equation
[OH-:1].[K+].[CH3:3][O:4][C:5]1[CH:35]=[CH:34][C:8]([O:9][CH:10]2[CH2:13][N:12]([C:14]([CH3:33])([CH3:32])[CH2:15][CH2:16][C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:18]#[N:19])[CH2:11]2)=[CH:7][CH:6]=1>CC(O)(CC)CC>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH:10]2[CH2:11][N:12]([C:14]([CH3:32])([CH3:33])[CH2:15][CH2:16][C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:18]([NH2:19])=[O:1])[CH2:13]2)=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59423972HCID 59423972, compound

Product 1

HCID 59423907HCID 59423907, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 64933-Methyl-3-pentanolSolvent

Procedure

Potassium hydroxide (135 mg, 2.41 mmol) was added to a solution of the product of example 105 (53 mg, 0.12 mmol) in 3-methyl-3-pentanol (5 mL) and the mixture was heated under reflux for 18 hours. The reaction mixture was then cooled to room temperature, concentrated in vacuo and the residue was partitioned between ethyl acetate (20 mL) and water (5 mL). The aqueous layer was separated, extracted with ethyl acetate (2×20 mL) and the combined organic solution was dried over magnesium sulfate and concentrated in vacuo to give a colourless oil in 96% yield, 53 mg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate (20 mL) and water (5 mL)
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate (2×20 mL)
  7. dry with materialthe combined organic solution was dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a colourless oil in 96% yield, 53 mg

Sources & evidence

ORD record
ord-a188a058983b426fb5502661f0708c00
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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