18227-62-8

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 2814, 1955 DOI: 10.1021/ja01615a042

Upstream product

• 17153-02-5 rac-4-acetyl-4-methyl-2-phenyloxazol-5-one 
• 50996-03-7 benzamidoacetone 
• 74-88-4 methyl iodide 
• 133957-65-0 N-(but-3-en-2-yl)-benzamide 
• 2198-64-3 N-Benzoylalanine 
• 51127-13-0 2-phenyl-4-methyl-4H-oxazolin-5-one 
• 17153-00-3 5-acetyloxy-4-methyl-2-phenyloxazole 
• 98-88-4 benzoyl chloride 
• 108-24-7 acetic anhydride 
• 917-54-4 methyllithium 
• 506-96-7 Acetyl bromide 
• 20662-83-3 4,5-dimethyl-oxazole 

Downstream Products

• 1826-24-0 4,5-dimethyl-2-phenyl-1,3-thiazole 
• 37557-72-5 3-benzamido-3-methylbutan-2-one 
• 90127-53-0 2-phenyl-4,5-bis(bromomethyl)oxazole 
• 21419-24-9 3-Amino-2-butanone hydrochloride 
• 26028-53-5 4,5-dimethyl-2-phenyl-oxazole 

Relevant academic research and scientific papers

Aldehyde selective Wacker oxidations of phthalimide protected allylic amines: A new catalytic route to β3-amino acids

(Chemical Equation Presented) A new method for the synthesis of β3-amino acids is presented. Phthalimide protected allylic amines are oxidized under Wacker conditions selectively to aldehydes using PdCl2 and CuCl or Pd(MeCN)2/s

Pyrrolomorphinans as δ opioid receptor antagonists. The role of steric hindrance in conferring selectivity

A series of 2',3'-disubstituted pyrrolomorphinans (5a-i) were synthesized to determine the role of steric hindrance at μ and γ receptors in promoting δ opioid receptor antagonist selectivity. In smooth muscle preparations, five members of the series (5a-c,e,f) possessed K(e) values in the range 2-15 nM and were 6 selective. Since the unsubstituted analogue 4 possessed δ antagonist potency of similar magnitude, but was not δ selective, it is suggested that the 2',3'substitution confers δ selectivity by hindering the interaction of the pharmacophore at μ and γ receptors, while not affecting δ receptors.

A versatile synthesis of 3-phenylsulfonylpyrroles from α-amino acids

Reaction between α-benzamidoalkyl ketones 4a-e and the vinyl phosphonium salt 1 produces 3-phenylthio-3-pyrrolines 5a-e which can be converted into N-benzyl-3-phenylsulfonyl pyrroles 7a-e by m-CPBA oxidation, diborane reduction and DDQ aromatisation.

AMIDOACETONE ENOLATE ANIONS: ALKYLATION AND MICHAEL REACTION

The lithyum enolate derived from benzamidoacetone (1) can be regiospecifically alkylated at C(1) and stereospecifically added in conjugate fashion to cyclohexenone without resorting to protection of free NH.Comparison is made with alkylations of methyl hippurate.