Water → HCID 90413169, compound

HRID 1522010Notes

Reaction equation

HRID 1522010 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([NH:9]C(=O)C(C)(C)C)[C:3]=1[C:16]#[C:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.C1OCCOCCOCCOCCOCCOC1.CC([O-])(C)C.[K+].O>C(O)(C)(C)C>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][C:17]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)=[CH:16][C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 90412447HCID 90412447, compound

Product 1

HCID 90413169HCID 90413169, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of Example 255A (1000 mg, 2.283 mmol), 18-crown-6 (302 mg, 1.142 mmol), and potassium 2-methylpropan-2-olate (512 mg, 4.57 mmol) in 15 mL t-butanol was heated under microwave (Biotage) conditions at 135° C. for 35 minutes. Water was added and the mixture was extracted with dichloromethane. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was triturated with diethyl ether and filtered to afford the title compound. MS (ESI(+)) m/e 354 (M+H)+.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-95fa46e765e14aa190ef60eabe2306ba
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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