Ammonia → HCID 68620036, compound

HRID 1725568Notes

Reaction equation

HRID 1725568 reaction equation
[CH3:1][CH:2]([C:14](=O)[CH3:15])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>C(OCC)C>[CH2:6]([NH:5][C:3](=[O:4])[C:2]([CH3:1])=[C:14]([NH2:17])[CH3:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6451240Aluminum(III) ChlorideHCID 119843462-methyl-3-oxo-N-phenethyl-butyramide

Product 1

HCID 68620036HCID 68620036, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-methyl-3-oxo-N-phenethyl-butyramide of Example 1d (1.10 g, 5.00 mmol) in diethyl ether (300 mL) was saturated with gaseous ammonia for 3 h while cooled in an ice bath. Anhydrous aluminum chloride (99.99% purity, 0.667 g, 5.00 mmol) was then added in small portions and the reaction was allowed to stir at room temperature overnight. The reaction mixture was filtered and concentrated under reduced pressure to give 3-amino-2-methyl-but-2-enoic acid phenethyl-amide (0.97 g, 85% conversion by NMR) as a white solid which was used without purification for the next synthetic step.

Workup

  1. temperaturewhile cooled in an ice bath
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1aac1e4bce847a19f7a67e3232eeced
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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