Water → HCID 53842782, compound

HRID 726872Notes

Reaction equation

HRID 726872 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[C:4]([NH2:6])=[O:5].[C:10]1([C@@H:16]([NH2:18])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=[N:18][C@H:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:17])[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 758181-Phenethylamine, (-)-HCID 12922742Trimethylpyruvic acid amide

Product 1

HCID 53842782HCID 53842782, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 35.0 g (271 mmol) of 3,3-dimethyl-2-oxobutyramide and 75.0 g (619 mmol) of (S)-1-phenylethylamine in 250 ml of toluene was boiled under reflux on a water separator for 92 hours. Subsequently, the solvent and excess amine were removed in a vacuum. The residual oil was crystallized from 300 ml of hexane. 51 g of crude material of melting point 96°-97° C. were obtained. After recrystallization from 400 ml of hexane there were obtained 42.7 g (68%) of analytically-pure (S)-3,3-dimethyl-2-(1-phenylethylimino)-butyramide of melting point 100°-101° C. [α]=-58.5 (c=1.0, CHCl3).

Workup

  1. customSubsequently, the solvent and excess amine were removed in a vacuum
  2. customThe residual oil was crystallized from 300 ml of hexane
  3. custom51 g of crude material of melting point 96°-97° C. were obtained
  4. customAfter recrystallization from 400 ml of hexane

Sources & evidence

ORD record
ord-26ec7719187b498bbaee65dbdfa3a5c8
Source dataset
uspto-grants-1998_01
Patent number
US05710322

Reaction notes

Loading…