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Potassium tert-butoxide → HCID 69318521, compound

HRID 2410346
Notes
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Reaction equation

HRID 2410346 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])[C:3]=1[C:13]([NH:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2([C:31]([O:33][CH3:34])=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH2:20][CH2:19]1)=[N:14][OH:15].CC(C)([O-])C.[K+]>CN1CCCC1=O.O>[CH2:9]([O:8][C:4]1[C:3]2[C:13]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([CH2:24][C:25]4([C:31]([O:33][CH3:34])=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH2:20][CH2:19]3)=[N:14][O:15][C:2]=2[CH:7]=[CH:6][CH:5]=1)[CH:10]([CH3:12])[CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178498707HCID 178498707, compound

Product 1

HCID 69318521HCID 69318521, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-{[4-({[(2-fluoro-6-isobutoxyphenyl)(hydroxyimino)methyl]amino}methyl)-piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (0.84 g, 1.8 mmol, EXAMPLE 16, Step 8) in N-methylpyrrolidone (9.0 mL) was added potassium tert-butoxide (0.22 g, 2.0 mmol) at room temperature. The mixture was heated at 100° C. for 5 h and cooled to room temperature. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL×2) and washed with water (50 mL). The combined extracts were dried over magnesium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 1:1 to 1:2) to give 0.30 g (36%) of the title compound as a colorless viscous oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (50 mL×2)
  3. washwashed with water (50 mL)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThe residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 1:1 to 1:2)

Sources & evidence

ORD record
ord-30d7dfc0c2e04ee1921f4e3033d6b54e
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08816090B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes