2-{[(1S,2S)-1-Hy-droxy-1-phenyl-propan-2-yl](methyl)amino}-N-(3-methyl-phen-yl)acetamide

Area of Science:

• Organic Chemistry
• Crystallography
• Chirality Studies

Background:

• Synthesis of novel organic compounds is crucial for materials science and medicinal chemistry.
• Understanding the three-dimensional structure of chiral molecules is essential for predicting their properties and interactions.

Purpose of the Study:

• To synthesize and characterize a new organic compound, m-TAP.
• To determine the crystal structure and absolute configuration of m-TAP.

Main Methods:

• Chemical synthesis involving the reaction of 2-chloro-N-(m-tolyl)acetamide with pseudoephidrine.
• Single crystal X-ray diffraction analysis to elucidate the crystal system, space group, and molecular geometry.
• Analysis of chiral centers and their absolute configurations.

Main Results:

• The title compound, C19H24N2O2 (m-TAP), was successfully synthesized.
• m-TAP crystallizes in the monoclinic crystal system within the chiral space group P21 (No. 4).
• The crystal structure features a dihedral angle of 89.20 (10)° between phenyl rings, and two chiral centers (C7 and C8) with an absolute S configuration.

Conclusions:

• The synthesis and structural determination of m-TAP provide valuable data for organic chemistry and crystallography.
• The non-centrosymmetric chiral nature of m-TAP, with defined S configurations at two chiral centers, is established.
• This study contributes to the understanding of molecular structure-property relationships in chiral organic compounds.