327623-37-0

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R)-2-((S)-1-(3,5-bis(trifluoroMethyl)phenyl)ethoxy)-3-(4-fluorophenyl)Morpholine is used as an impurity in Aprepitant (A729800), a novel selective neurokinin-1 (NK-1) receptor antagonist. It plays a crucial role in the development and manufacturing process of Aprepitant, ensuring the purity and efficacy of the drug.
Used in Antiemetic Applications:
As an impurity of Aprepitant, (2S,3R)-2-((S)-1-(3,5-bis(trifluoroMethyl)phenyl)ethoxy)-3-(4-fluorophenyl)Morpholine contributes to the antiemetic properties of the drug. Aprepitant is primarily used to prevent nausea and vomiting associated with chemotherapy, radiation therapy, and surgery. Its selective action on the NK-1 receptor helps to block the transmission of signals that trigger these symptoms.
Used in Metabolism Studies:
In vitro studies using human liver microsomes have shown that Aprepitant is metabolized primarily by CYP3A4, with minor metabolism by CYP1A2 and CYP2C19. The presence of (2S,3R)-2-((S)-1-(3,5-bis(trifluoroMethyl)phenyl)ethoxy)-3-(4-fluorophenyl)Morpholine in Aprepitant may provide insights into the drug's metabolism and potential drug-drug interactions, further enhancing its therapeutic applications.

Upstream product

• 1523569-82-5 C₂₇H₂₂F₇NO₃ 
• 1523569-83-6 C₂₈H₂₄F₇NO₂ 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 447-43-8 1-(4-fluorophenyl)-2,2-dihydroxyethan-1-one 
• 934540-47-3 C₂₀H₁₆F₇NO₂ 

Downstream Products

• 172822-29-6 5-[{(2S,3R)-2-((1S)-1-3,5-bis(trifluoro-methyl)phenylethoxy)-3-(4-fluorophenyl)-4-morpholinyl}methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one 

Relevant academic research and scientific papers

Preparation method of NK1 receptor antagonist

The invention discloses a preparation method of an NK1 receptor antagonist. According to the invention, chiral resolution adopts a mixed solvent, CaCl2 is added for a reaction in an alkaline environment, CaCl2 does not participate in the reaction but needs to be added in advance for better devitrification, water is added for quenching after the reaction is finished, and CaCl2 is dissolved at the same time, so devitrification efficiency is further improved; and then 5-hydroxymethyl-2,4-dihydro-[1,2,4]triazin-3-one is used as a raw material for synthesis of aprepitant under the catalysis of DBU at room temperature.

Synthesis of the major isomers of Aprepitant and Fosaprepitant

The synthesis of two isomers of Aprepitant (APT) and three isomers of Fosaprepitant (FPT), crucial components for quality control in manufacturing, is described. Herein, three chiral centers in the isomers of Aprepitant are established in high yield by in

Synthesis of all enantiomerically pure diastereomers of aprepitant

Syntheses of all eight enantiomerically pure diastereomers of aprepitant and assignment of absolute configuration at newly generated stereocenters by NMR and X-ray crystallographic analysis were achieved. Copyrigh

PREPARATION OF APREPITANT

A process for preparing aprepitant.