Potassium Hydroxide → HCID 59423877, compound

HRID 2387678Notes

Reaction equation

HRID 2387678 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[O:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]([CH3:32])([CH3:31])[CH2:14][CH2:15][C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]#[N:18])[CH2:9]1>CC(O)(CC)CC>[Cl:3][C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[O:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]([CH3:32])([CH3:31])[CH2:14][CH2:15][C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]([NH2:18])=[O:1])[CH2:9]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59423885HCID 59423885, compound

Product 1

HCID 59423877HCID 59423877, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 64933-Methyl-3-pentanolSolvent

Procedure

Potassium hydroxide (140 mg, 2.49 mmol) was added to a solution of the product of example 27 (61 mg, 0.125 mmol) in 3-methyl-3-pentanol (5 mL) and the mixture was heated under reflux for 16 hours. The solution was cooled to room temperature, concentrated in vacuo and the residue was partitioned between dichloromethane (10 mL) and water (5 mL), aqueous was extracted with dichloromethane (3×10 mL). Combined organics were concentrated under reduced pressure and the residue purified by column chromatography on silica gel, eluting with ethyl acetate:methanol:0.88 ammonia, 90:10:1. The product containing fractions were evaporated under reduced pressure to afford the title compound as a colourless gum in 33% yield, 21 mg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between dichloromethane (10 mL) and water (5 mL)
  5. extractionaqueous was extracted with dichloromethane (3×10 mL)
  6. concentrationCombined organics were concentrated under reduced pressure
  7. customthe residue purified by column chromatography on silica gel
  8. washeluting with ethyl acetate
  9. additionThe product containing fractions
  10. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-235ae43433a047289c99898ebd87cd4b
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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