[(3R)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid

Base Information

• Chemical Name: [(3R)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid
• CAS No.: 1234474-57-7
• Molecular Formula: C₂₉H₃₂O₇S
• Molecular Weight: 524.635

Synonyms:[(3R)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid

Chemical Property of [(3R)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

(R)-(-)-TAK-875 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (R)-(-)-TAK-875 is the R-isomer of TAK-875 (T004915); a potent, selective, and orally bioavailable GPR40 agonist.

Technology Process of [(3R)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid

There total 24 articles about [(3R)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid 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:

[6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-1-benzofuran-3-yl]acetic acid (1394138-50-1) → [(3S)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid (1000413-72-8) + [(3R)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid (1234474-57-7,1000413-72-8)

Guidance literature:

With hydrogen; triethylamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; (R)-1-[(S)-2-[bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl]ethyldi-tert-butylphosphine; In tetrahydrofuran; methanol; at 50 ℃; for 24h; under 7500.75 Torr; Product distribution / selectivity; Autoclave;

Reference yield:

2-bromo-5-(3-methanesulfonyl-propoxy)-1,3-dimethyl-benzene (1372195-69-1) → [(3R)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid (1234474-57-7,1000413-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium phosphate / triphenylphosphine; palladium diacetate; tetrabutylammomium bromide / tetrahydrofuran / 8 h / Reflux; Inert atmosphere

2.1: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 25 °C

3.1: potassium phosphate / N,N-dimethyl-formamide / 3 h / 70 °C

4.1: sodium hydroxide; water / dimethyl sulfoxide / 21 h / 25 - 70 °C

4.2: pH 1 - 2

5.1: triethylamine; hydrogen / [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; (R)-1-[(S)-2-(di-p-fluorophenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine / tetrahydrofuran; methanol / 24 h / 50 °C / 7500.75 Torr / Autoclave

With potassium phosphate; water; hydrogen; triethylamine; sodium hydroxide; trichlorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; (R)-1-[(S)-2-(di-p-fluorophenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; tetrabutylammomium bromide; palladium diacetate; N,N-dimethyl-formamide; triphenylphosphine; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

[3-(hydroxymethyl)phenyl]boronic acid (87199-15-3) → [(3R)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid (1234474-57-7,1000413-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium phosphate / triphenylphosphine; palladium diacetate; tetrabutylammomium bromide / tetrahydrofuran / 8 h / Reflux; Inert atmosphere

2.1: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 25 °C

3.1: potassium phosphate / N,N-dimethyl-formamide / 3 h / 70 °C

4.1: sodium hydroxide; water / dimethyl sulfoxide / 21 h / 25 - 70 °C

4.2: pH 1 - 2

5.1: triethylamine; hydrogen / [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; (R)-1-[(S)-2-(di-p-fluorophenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine / tetrahydrofuran; methanol / 24 h / 50 °C / 7500.75 Torr / Autoclave

With potassium phosphate; water; hydrogen; triethylamine; sodium hydroxide; trichlorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; (R)-1-[(S)-2-(di-p-fluorophenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; tetrabutylammomium bromide; palladium diacetate; N,N-dimethyl-formamide; triphenylphosphine; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

4-chloromethyl-7-hydroxycoumarin

recorcinol

[3-(hydroxymethyl)phenyl]boronic acid

(6-hydroxy-benzofuran-3-yl)-acetic acid methyl ester

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