Water → HCID 10871416, compound

HRID 726867Notes

Reaction equation

HRID 726867 reaction equation
[CH3:1][C:2]([CH3:11])([CH3:10])[C:3](=O)[C:4]([O:6]CC)=O.[C:12]1([C@@H:18]([NH2:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C1(C)C(C)=CC=CC=1>[CH3:11][C:2]([CH3:1])([CH3:10])[C:3](=[N:20][C@H:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:19])[C:4]([NH:20][C@H:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:19])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 758181-Phenethylamine, (-)-HCID 220085ethyl 3,3-dimethyl-2-oxobutanoate

Product 1

HCID 10871416HCID 10871416, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 15 g (95 mmol) of ethyl trimethyl-pyruvate and 50 g (413 mmol) of (S)-1-phenylethylamine in 50 ml of xylene was boiled under reflux on a water separator for 18 hours. Subsequently, the solvent was distilled off and excess amine was removed at 120° C. in a vacuum. After crystallization of the distillation residue from 125 ml of hexane there were obtained 14.3 g (45%) of (S)-3,3-dimethyl-N-[(S)-1-phenylethyl]-2-(1-phenylethylimino)-butyramide of melting point 96°-97° C. [α]=-58.9 (c=1.0, CHCl3).

Workup

  1. distillationSubsequently, the solvent was distilled off
  2. customexcess amine was removed at 120° C. in a vacuum
  3. customAfter crystallization of the distillation residue from 125 ml of hexane

Sources & evidence

ORD record
ord-23ba930ea1634e12816ffa93b230c82e
Source dataset
uspto-grants-1998_01
Patent number
US05710322

Reaction notes

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