Potassium tert-butoxide → HCID 68426445, compound

HRID 642558Notes

Reaction equation

HRID 642558 reaction equation
C(O[C:4]([C:6]1[S:10][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:8][C:7]=1[CH2:15][N:16]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][CH3:33])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:5])C.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[CH2:21]([O:20][C:18]([CH:17]1[N:16]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])[CH2:15][C:7]2[N:8]=[C:9]([C:11]([CH3:13])([CH3:14])[CH3:12])[S:10][C:6]=2[C:4]1=[O:5])=[O:19])[CH3:22]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 68428986HCID 68428986, compound

Product 1

HCID 68426445HCID 68426445, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-tert-butyl-4-{[(2,4-dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-thiazole-5-carboxylic acid ethyl ester (12.8 g, 26.7 mmol) in 350 mL of anhydrous THF was cooled to 0° C. with an external ice bath and 53 mL of 1 N potassium tert-butoxide was added slowly. The reaction was stirred at 0° C. for 2 h and then allowed to warm to room temperature and stirred for 2 h. The reaction was diluted with ethyl acetate and washed with a solution of 200 mL saturated ammonium chloride and 50 mL 1 N HCl. The organic fraction was washed with brine, dried over anhydrous sodium sulfate and concentrated to 11.5 g of product. MS (ESI+): m/z 433.4 (M+1).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 h
  3. washwashed with a solution of 200 mL saturated ammonium chloride and 50 mL 1 N HCl
  4. washThe organic fraction was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to 11.5 g of product

Sources & evidence

ORD record
ord-0c14613562b443db87b68a8a76dcd39b
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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