(E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester
• CAS No.: 188557-38-2
• Molecular Formula: C₂₃H₂₈FNO₆S
• Molecular Weight: 465.543
• Mol file: 188557-38-2.mol

Synonyms:(E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester

Chemical Property of (E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester

There total 17 articles about (E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester 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: 97.6%

(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester (160204-82-0) → (E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester (188557-38-2)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 1.5h; Ambient temperature;

DOI:10.1016/S0968-0896(96)00248-9

Reference yield:

(S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester (109721-08-6) → (E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester (188557-38-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -30 - 2 °C

1.2: 100 percent / tetrahydrofuran; hexane / 0.92 h / -66 - -30 °C

2.1: 74 percent / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 0.92 h / 0 - 15 °C

3.1: 98 percent / methanol / 0.53 h / 0 °C

4.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 °C

4.2: 1.98 g / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / 0 °C

5.1: 91 percent / toluene / 1 h / Heating

6.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.2: 62 percent / tetrahydrofuran / 6 h / -78 - 0 °C

7.1: 81 percent / aq. HF / acetonitrile / 1 h / 20 °C

With n-butyllithium; hydrogen fluoride; potassium tert-butylate; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 1.1: Metallation / 1.2: Acylation / 2.1: Cyclization / 3.1: Ring cleavage / 4.1: Metallation / 4.2: Condensation / 5.1: Elimination / 6.1: Metallation / 6.2: mesylation / 7.1: desilylation;

DOI:10.1021/jo9722156

Reference yield:

3-(4-fluoro-phenyl)-5-isopropyl-2-methyl-1H-pyrrole → (E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester (188557-38-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: CH₂Cl₂ / 1 h / Heating

2.1: CH₂Cl₂ / 0.5 h / 20 °C

3.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 °C

3.2: 1.98 g / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / 0 °C

4.1: 91 percent / toluene / 1 h / Heating

5.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

5.2: 62 percent / tetrahydrofuran / 6 h / -78 - 0 °C

6.1: 81 percent / aq. HF / acetonitrile / 1 h / 20 °C

With hydrogen fluoride; potassium tert-butylate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 1.1: Alkylation / 2.1: Methylation / 3.1: Metallation / 3.2: Condensation / 4.1: Elimination / 5.1: Metallation / 5.2: mesylation / 6.1: desilylation;

DOI:10.1021/jo9722156

upstream raw materials:

(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester

(S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester

(4R)-[(tert-butyldimethylsilyl)oxy]-6-[(methanesulfinyl)methylene]tetrahydropyran-2-one

(3R)-[(tert-butyldimethylsilyl)oxy]-6-(methanesulfinyl)-5-oxohexanoic acid methyl ester

Downstream raw materials:

(3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester