Ethyl 4-[(1,1-dimethylethyl)(2-ethoxy-2-oxoethyl)amino]butanoate → HCID 22228430, compound

HRID 1744693Notes

Reaction equation

HRID 1744693 reaction equation
[C:1]([N:5]([CH2:14][C:15]([O:17]CC)=O)[CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>O1CCCC1>[C:1]([N:5]1[CH2:6][CH2:7][CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:15](=[O:17])[CH2:14]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 22228401Ethyl 4-[(1,1-dimethylethyl)(2-ethoxy-2-oxoethyl)amino]butanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22228430HCID 22228430, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of step B (14.0 g; 50.9 mmol) in tetrahydrofuran (200 mL) was added 1.05 eq of potassium tert-butoxide (6.0 g; 53.5 mmol). The reaction was maintained at ambient temperature for 2 h and then quenched with a sufficient amount of saturated aqueous ammonium chloride to make the solution pH 8. The tetrahydrofuran was removed in vacuo and the aqueous layer was extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (7.15 g).

Workup

  1. customquenched with a sufficient amount of saturated aqueous ammonium chloride
  2. customThe tetrahydrofuran was removed in vacuo
  3. extractionthe aqueous layer was extracted three times with diethyl ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f62717219e7540b8919ef7568fe0faab
Source dataset
uspto-grants-2006_03
Patent number
US07015235B2

Reaction notes

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