865233-36-9

Basic information

• Product Name: (3S)-3-(4-Hydroxy-phenyl)-hex-4-ynoic acid methyl ester
• Synonyms: (3S)-3-(4-Hydroxy-phenyl)-hex-4-ynoic acid methyl ester;(S)-methyl 3-(4-hydroxyphenyl)hex-4-ynoate
• CAS NO: 865233-36-9
• Molecular Formula: C₁₃H₁₄O₃
• Molecular Weight: 218.24846
• EINECS: -0
• Mol File: 865233-36-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S)-3-(4-Hydroxy-phenyl)-hex-4-ynoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3-(4-Hydroxy-phenyl)-hex-4-ynoic acid methyl ester(865233-36-9)
• EPA Substance Registry System: (3S)-3-(4-Hydroxy-phenyl)-hex-4-ynoic acid methyl ester(865233-36-9)

Safety Data

• Hazardous Substances Data: 865233-36-9(Hazardous Substances Data)

Usage

Description

(3S)-3-(4-hydroxy-phenyl)-hex-4-ynoic acid methyl ester is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutical agents. It is characterized by its unique molecular structure, which includes a 3S stereochemistry, a 4-hydroxyphenyl group, and a hex-4-ynoic acid methyl ester functional group. (3S)-3-(4-hydroxy-phenyl)-hex-4-ynoic acid methyl ester plays a crucial role in the development of new drugs and therapeutic agents.

Uses

Used in Pharmaceutical Industry:
(3S)-3-(4-hydroxy-phenyl)-hex-4-ynoic acid methyl ester is used as a reagent in the synthesis of GPR40 agonists, which are potential antidiabetic agents. These agonists have the ability to stimulate the GPR40 receptor, a G-protein coupled receptor expressed in pancreatic β-cells, leading to increased insulin secretion and improved glucose tolerance in diabetic patients. The development of such agents can provide a novel approach to managing type 2 diabetes and its associated complications.

Upstream product

• 74-88-4 methyl iodide 
• 865233-35-8 (3S)-3-(4-hydroxy-phenyl)-hex-4-ynoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 865233-33-6 (+/-)-5-[1-(4-hydroxy-phenyl)-but-2-ynyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 865233-34-7 4-hydroxy-β-1-propyn-1-ylbenzenepropanoic acid 
• 1092773-21-1 (3S)-3-(4-hydroxyphenyl)hex-4-ynoic acid (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol salt 
• 865233-82-5 2,2-Dimethyl-5-[4-(tetrahydro-pyran-2-yloxy)-benzylidene]-[1,3]dioxane-4,6-dione 
• 1291087-13-2 C₁₈H₁₈O₆ 
• 17474-27-0 5-(4-hydroxy-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 123-08-0 4-hydroxy-benzaldehyde 
• 67-56-1 methanol 
• 865234-02-2 methyl 3-(4-hydroxyphenyl-1-propynyl)propanoate 
• 1146212-20-5 acetic acid 4-(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-ylidenemethyl)-phenyl ester 

Downstream Products

• 929713-35-9 (3S)-methyl 3-(4-(5-bromo-2,3-dihydro-1H-inden-1-yloxy)phenyl)hex-4-ynoate 
• 865233-37-0 (3S)-3-[4-(4'-trifluoromethyl-biphenyl-3-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester 
• 865231-46-5 [3H]-AMG 837 
• 865233-35-8 (3S)-3-(4-hydroxy-phenyl)-hex-4-ynoic acid 
• 929713-37-1 C₂₂H₂₂O₃ 

Relevant articles and documents

3-PHENYL-4-HEXYNOIC ACID DERIVATIVES AS GPR40 AGONISTS

A compound of the formula (I)wherein R represents a straight or branched, primary or secondary acyclic hydrocarbyl C3–C15 group, which can be saturated or unsaturated, or a straight or branched, primary or secondary acyclic hydrocarbyl C3–C15 group, which can be saturated or unsaturated and wherein one or more of hydrogen atoms is replaced with fluorine atom; X represents hydrogen atom or halogen atom,and* denotes chiral center, and salts thereof. The compound is useful for the treatment of diseases mediated by GPR40, in particular type II diabetes. (I)

ANTIDIABETIC BICYCLIC COMPOUNDS

Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

Development of a scalable synthesis of a GPR40 receptor agonist

Early process development and salt selection for AMG 837, a novel GPR40 receptor agonist, is described. The synthetic route to AMG 837 involved the convergent synthesis and coupling of two key fragments, (S)-3-(4-hydroxyphenyl) hex-4-ynoic acid (1) and 3-