Sodium Bicarbonate → Ethyl N-(2,3-dimethyl-2-isopropyl-1-oxobutyl)glycinate

HRID 848589Notes

Reaction equation

HRID 848589 reaction equation
C(=O)(O)[O-].[Na+].Cl.[CH2:7]([O:9][C:10](=[O:13])[CH2:11][NH2:12])[CH3:8].[CH3:14][C:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[C:16](Cl)=[O:17]>O.CCOCC>[CH2:7]([O:9][C:10](=[O:13])[CH2:11][NH:12][C:16](=[O:17])[C:15]([CH3:14])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[CH3:8]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 30166072,3-Dimethyl-2-isopropylbutyryl chloride

Product 1

HCID 6452343Ethyl N-(2,3-dimethyl-2-isopropyl-1-oxobutyl)glycinate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium bicarbonate (1.7 g, 0.02 mole) and glycine ethyl ester hydrochloride (1.4 g, 0.01 mole) were dissolved in water (10 ml) and a solution of 2,3-dimethyl-2-isopropylbutanoyl chloride (1.6 g, 0.009 mole) in ether (10 ml) was added. The mixture was stirred vigorously at room temperature for 2 hours. After 16 hours at room temperature the ether layer was separated and dried (MgSO4). Removal of the solvent left a white solid which was recrystallised from ether/petroleum ether to give N-(2,3-dimethyl-2-isopropylbutanoyl)glycine ethyl ester, mp. 74.5°-75.5°.

Workup

  1. customAfter 16 hours at room temperature the ether layer was separated
  2. dry with materialdried (MgSO4)
  3. customRemoval of the solvent
  4. waitleft a white solid which
  5. customwas recrystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-790d24fe12e946e6a4cd5825d5835508
Source dataset
uspto-grants-1981_10
Patent number
US04296255

Reaction notes

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