(3S)-3-(4-hydroxyphenyl)-hex-4-ynoic acid (1S,2R)-1-amino-2-indanol salt

Base Information

• Chemical Name: (3S)-3-(4-hydroxyphenyl)-hex-4-ynoic acid (1S,2R)-1-amino-2-indanol salt
• CAS No.: 1092773-21-1
• Molecular Formula: C₉H₁₁NO*C₁₂H₁₂O₃
• Molecular Weight: 353.418
• Mol file: 1092773-21-1.mol

Synonyms:(3S)-3-(4-hydroxyphenyl)hex-4-ynoic acid (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol salt

Chemical Property of (3S)-3-(4-hydroxyphenyl)-hex-4-ynoic acid (1S,2R)-1-amino-2-indanol salt

Chemical Property:

• Melting Point: 202-203 °C

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-(4-hydroxyphenyl)-hex-4-ynoic acid (1S,2R)-1-amino-2-indanol salt

There total 9 articles about (3S)-3-(4-hydroxyphenyl)-hex-4-ynoic acid (1S,2R)-1-amino-2-indanol salt which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

4-hydroxy-β-1-propyn-1-ylbenzenepropanoic acid (865233-34-7) + (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8) → (3S)-3-(4-hydroxyphenyl)hex-4-ynoic acid (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol salt (1092773-21-1)

Guidance literature:

In acetonitrile; at 70 ℃; for 4h;

Reference yield:

4-hydroxy-β-1-propyn-1-ylbenzenepropanoic acid (865233-34-7) + (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8) → C9H11NO*C12H12O3 + (3S)-3-(4-hydroxyphenyl)hex-4-ynoic acid (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol salt (1092773-21-1)

Guidance literature:

In isopropyl alcohol; at 20 - 70 ℃; for 16h; Resolution of racemate;

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → (3S)-3-(4-hydroxyphenyl)hex-4-ynoic acid (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol salt (1092773-21-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: water; toluene / 4.67 h / 23 - 33 °C / Large scale reaction

2.1: 4-methyl-morpholine / tetrahydrofuran / 0.5 h / 25 °C / Large scale reaction

3.1: tetrahydrofuran / 0.5 h / 25 °C / Large scale reaction

4.1: sodium hydroxide / water / 25 - 50 °C / Large scale reaction

5.1: water; N,N-dimethyl-formamide / 1.5 h / 100 °C

6.1: acetonitrile / 4 h / 65 - 70 °C

6.2: 3.5 h / 20 - 70 °C

With 4-methyl-morpholine; sodium hydroxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Knoevenagel condensation;

DOI:10.1021/op1003055

upstream raw materials:

4-hydroxy-β-1-propyn-1-ylbenzenepropanoic acid

(1S,2R)-1-amino-2-indanol

acetic acid 4-(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-ylidenemethyl)-phenyl ester

(+/-)-5-[1-(4-hydroxy-phenyl)-but-2-ynyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Downstream raw materials:

(3S)-3-[4-(4'-trifluoromethyl-biphenyl-3-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester

[3H]-AMG 837

(3S)-3-(4-hydroxy-phenyl)-hex-4-ynoic acid methyl ester

(3S)-3-(4-hydroxy-phenyl)-hex-4-ynoic acid