Hydrochloric Acid → Ethyl 2-amino-2-ethylbutanoate

HRID 1436066Notes

Reaction equation

HRID 1436066 reaction equation
C1(C(=[N:14][C:15]([CH2:23][CH3:24])([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.Cl>C(OCC)C.C([O-])(O)=O.[Na+]>[NH2:14][C:15]([CH2:21][CH3:22])([CH2:23][CH3:24])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10805871HCID 10805871, compound

Product 1

HCID 437603Ethyl 2-amino-2-ethylbutanoateYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of ethyl 2-[(diphenylmethylene)amino]-2-ethylbutanoate (20.79 g, 64.3 mmol), prepared in the previous step, in 200 mL of diethyl ether was cooled under nitrogen to ice-bath temperature. 1 N HCl (96 mL, 96.0 mmol) was added dropwise over 45 min. After the addition, the ice-bath was removed and the stirring continued for 15 h. The diethyl ether layer was separated and the aqueous layer was extracted two times with 50 mL of methylene chloride. The methylene chloride extracts were extracted two times with 40 mL of 2 N HCl. The aqueous layers were combined and concentrated under reduced pressure to give an oil. The oil was taken up in 200 mL of saturated NaHCO3 and stirred for 30 min. The aqueous layer was then extracted five times with methylene chloride. The organic extracts were dried (anhydrous MgSO4), filtered and the solvent removed under reduced pressure to give ethyl 2-amino-2-ethylbutanoate (9.3799 g, 92%) as a yellow liquid.

Workup

  1. temperaturewas cooled under nitrogen to ice-bath temperature
  2. additionAfter the addition
  3. customthe ice-bath was removed
  4. customThe diethyl ether layer was separated
  5. extractionthe aqueous layer was extracted two times with 50 mL of methylene chloride
  6. extractionThe methylene chloride extracts were extracted two times with 40 mL of 2 N HCl
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil
  9. extractionThe aqueous layer was then extracted five times with methylene chloride
  10. dry with materialThe organic extracts were dried (anhydrous MgSO4)
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-63f9b97dbfd04033b62fd3ffccccec0a
Source dataset
uspto-grants-2009_11
Patent number
US07618989B2

Reaction notes

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