Potassium tert-butoxide → HCID 178453869, compound

HRID 1521947Notes

Reaction equation

HRID 1521947 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]#[C:15][C:16]2[C:17]([NH:23]C(OC(C)(C)C)=O)=[N:18][CH:19]=[CH:20][C:21]=2[Cl:22])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[NH:23][C:17]3=[N:18][CH:19]=[CH:20][C:21]([Cl:22])=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178452981HCID 178452981, compound

Product 1

HCID 178453869HCID 178453869, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 74B (150 mg, 0.429 mmol) in N,N-dimethylformamide (5 mL) was treated with potassium tert-butoxide (122 mg, 1.085 mmol) and the mixture was stirred at room temperature for 12 hours. The mixture was quenched with ice water and extracted into ethyl acetate (30 mL×2). The organic layer was washed with water and brine solution (25 mL each) and the organic layer was separated, dried over sodium sulfate, filtered, and concentrated to afford the title compound. LCMS: 250.1 (M+H)+.

Workup

  1. customThe mixture was quenched with ice water
  2. extractionextracted into ethyl acetate (30 mL×2)
  3. washThe organic layer was washed with water and brine solution (25 mL each)
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8992a3c216284372941b4c0d25df3ba0
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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