Potassium tert-butoxide → HCID 68428251, compound

HRID 642386Notes

Reaction equation

HRID 642386 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]([C:35](O)=[O:36])=[C:14]([CH2:16][N:17]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[O:33][CH3:34])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1>[CH2:22]([O:21][C:19]([CH:18]1[N:17]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=2[O:33][CH3:34])[CH2:16][C:14]2[N:15]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])=[CH:6][CH:7]=3)[S:12][C:13]=2[C:35]1=[O:36])=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 68428248HCID 68428248, compound

Product 1

HCID 68428251HCID 68428251, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

2-(4-tert-Butyl-phenyl)-4-{[(2,4-dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-thiazole-5-carboxylic acid ethy este (1.11 g, 2.0 mmol) was dissolved in 21 mL of anhydrous THF and cooled to −15° C. in a brine dry ice bath. A solution of 4.4 mL of 1.0 M potassium tert-butoxide in THF was added slowly to cold solution, and the reaction was stirred at −15° C. for 30 min. and then at room temperature for 2 h. The reaction was quenched with 4.4 mL of 1N HCl and 150 mL of saturated ammonium chloride aqueous solution, and extracted twice with 150 mL of chloroform. The organic fractions were washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-70% ethyl acetate in hexanes to produce 0.5 g of a yellow froth. MS: (+) m/z 508.9 (M+1).

Workup

  1. waitat room temperature for 2 h
  2. customThe reaction was quenched with 4.4 mL of 1N HCl and 150 mL of saturated ammonium chloride aqueous solution
  3. extractionextracted twice with 150 mL of chloroform
  4. washThe organic fractions were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography
  8. washeluting from silica gel with a gradient of 0-70% ethyl acetate in hexanes
  9. customto produce 0.5 g of a yellow froth

Sources & evidence

ORD record
ord-bf5ba8631ce84fbdac8b60cb8e51ace6
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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