HCID 18694219, compound → HCID 10990514, compound

HRID 1870879Notes

Reaction equation

HRID 1870879 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)=[C:10]([CH3:24])[CH:9]=1)=[O:6].CC(C)([O-])C.[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:24][C:10]1[CH:9]=[C:8]([N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[CH:13]=[CH:12][C:11]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 18694219HCID 18694219, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10990514HCID 10990514, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4'-((4-chlorobutanoyl)amino)-2'-methylbiphenyl-4-carboxylate (D3) (1.65 g, 4.8 mmol) was stirred in dry dimethylformamide (DMF) (20 ml) as potassium t-butoxide (0.70 g, 5.7 mmol) was added. The mixture was stirred for 30 min, diluted with ethyl acetate (200 ml), washed successively with brine, water and brine, dried (Na2SO4) and evaporated to give a light brown gum. Chromatography on silica gel, eluting with 0-50% ether/dichloromethane, gave the title compound (1.15 g, 71%) as a light yellow solid.

Workup

  1. additionwas added
  2. washwashed successively with brine, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give a light brown gum
  6. washChromatography on silica gel, eluting with 0-50% ether/dichloromethane

Sources & evidence

ORD record
ord-df616f7af5f1430bbd495aac59c35208
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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