Trimethylpyruvic acid → HCID 54369426, compound

HRID 726869

Reaction equation

HRID 726869 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[CH:3]=[N:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].CC(C)(C)C(=O)[C:18]([OH:20])=[O:19]>C(OCC)C>[CH3:14][C:2]([CH3:13])([CH3:1])[C:3](=[N:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 13150Trimethylpyruvic acidHCID 10921316HCID 10921316, compound

Product 1

HCID 54369426HCID 54369426, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

8.9 g (47 mmol) of (S)-(2,2-dimethylpropylidene)-(1-phenylethyl)-amine (J. L. Fauchure, C. Petermann, Helv. Chim. Acta 1980, 63, 824) were dissolved in 10 ml of diethyl ether with the exclusion of moisture. 8.1 g (50 mmol) of trimethylpyruvic acid in 10 ml of diethyl ether were added dropwise to this solution while cooling with ice. Subsequently, the mixture was stirred at 0° C. for a further 2 hours and at room temperature for 6 hours. Colorless crystals form over 2 days and these were suspended in 50 ml of diethyl ether, filtered off and washed twice with 5 ml of diethyl ether each time. After drying in a vacuum there were obtained 8.9 g (81%) of (S)-3,3-dimethyl-2-(1-phenylethylimino)-butyric acid (internal salt) of melting point 135°-136° C. [α]=-14.4 (c=0.16, CH2Cl2).

Workup

  1. temperaturewhile cooling with ice
  2. customColorless crystals form over 2 days
  3. filtrationfiltered off
  4. washwashed twice with 5 ml of diethyl ether each time
  5. customAfter drying in a vacuum there

Sources & evidence

ORD record
ord-c251794771034e39bfe469d983ba6813
Source dataset
uspto-grants-1998_01
Patent number
US05710322

Linked notes

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