475200-52-3

Upstream product

• 2550-36-9 Cyclohexylmethyl bromide 
• 40187-51-7 5-acetylsalicylamide 
• 475200-38-5 (S)-methyl 2-(cyclohexylmethoxy)-5-(1-hydroxyethyl)benzoate 
• 260371-57-1 methyl 5-acetyl-2-(cyclohexylmethoxy)benzoate 
• 475200-46-5 2-Cyclohexylmethoxy-5-((S)-1-hydroxy-ethyl)-benzoic acid 
• 189393-76-8 5-acetyl-2-(cyclohexylmethoxy)benzamide 

Downstream Products

• 475200-55-6 5-((R)-1-Azido-ethyl)-2-cyclohexylmethoxy-benzamide 
• 475200-28-3 (R)-5-(1-aminoethyl)-2-(cyclohexylmethoxy)benzamide 

Relevant academic research and scientific papers

Efficient chemoenzymatic synthesis of (S)- and (R)-5-(1-aminoethyl)-2-(cyclohexylmethoxy)benzamide: Key intermediate for Src-SH2 inhibitor

A facile chemoenzymatic synthesis of both the S and R forms of 5-(1-aminoethyl)-2-(cyclohexylmethoxy)benzamide a key intermediate of non-peptidic Src SH2 inhibitors is described. Both the enantiomers were synthesized in high optical purity (>99% ee) by reduction followed by lipase-mediated acylation of the precursor 6 in one-pot. Immobilized Pseudomonas cepacia lipase offered high degree of enantioselectivity with spontaneity.

Synthesis of (S)-5-(1-aminoethyl)-2-(cyclohexylmethoxy)benzamide

Three short syntheses of the title compound, a peptidomimetic for the Glu-Glu-Ile-NH2 portion of Ac-pTyr-Glu-Glu-Ile-NH2, a high affinity peptide for the Src SH2 domain, are described. The most efficient route produces the title compound in a final enantiopurity of 94% ee. (C) 1999 Elsevier Science Ltd.