110862-46-9

Basic information

• Product Name: N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide
• Synonyms: 5-(4-Fluorophenyl)-2-(1-Methylethyl)-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxaMide;N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide;5-(4-fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxamide
• CAS NO: 110862-46-9
• Molecular Formula: C₂₉H₂₇FN₂O₂
• Molecular Weight: 454.5352832
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 110862-46-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide(110862-46-9)
• EPA Substance Registry System: N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxaMide(110862-46-9)

Safety Data

• Hazardous Substances Data: 110862-46-9(Hazardous Substances Data)

Usage

Description

N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxamide is a complex organic compound characterized by its white solid appearance. It is an intermediate in the synthesis of rac-3-Oxo Atorvastatin Sodium Salt (O847150), a compound used for treating metabolic diseases.

Uses

1. Used in Pharmaceutical Industry:
N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxamide is used as an intermediate in the synthesis of rac-3-Oxo Atorvastatin Sodium Salt (O847150) for the development of medications to treat metabolic diseases. Its role in the synthesis process is crucial for creating effective treatments that can help manage and alleviate the symptoms of these conditions.
2. Used in Metabolic Disease Treatment:
N-Phenyl-5-(4-Fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-4-phenyl-1H-pyrrole-3-carboxamide contributes to the creation of rac-3-Oxo Atorvastatin Sodium Salt (O847150), which is employed in the treatment of metabolic diseases. The compound plays a significant role in the development of pharmaceuticals that can improve the quality of life for patients suffering from such diseases by regulating their metabolic functions and providing relief from associated health issues.

Upstream product

• 110862-45-8 1-<2-(1,3-dioxolan-2-yl)ethyl>-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide 
• 110862-44-7 α-<<2-(1,3-dioxolan-2-yl)ethyl>(2-methyl-1-oxopropyl)amino>-4-fluorobenzeneacetic acid 
• 110862-43-6 α-<<2-(1,3-dioxolan-2-yl)ethyl>(2-methyl-1-oxopropyl)amino>-4-fluorobenzeneacetic acid, ethyl ester 
• 125971-96-2 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide 
• 124401-38-3 4-methyl-3-oxo-N-phenylpentanamide 
• 42558-54-3 Methyl 4-methyl-3-oxopentanoate 
• 62-53-3 aniline 
• 125971-57-5 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide 

Downstream Products

• 110862-47-0 methyl 7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate 
• 125971-63-3 (R^*,R^*)-3,5-dihydroxy-7-<(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-1-heptanoic acid 
• 110862-39-0 5-(4-Fluoro-phenyl)-1-[2-((2R,4S)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide 
• 110862-39-0 (+/-)-trans-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-<2-tetrahydro-4-hydroxy-6-oxo-2H-pyran-6-yl)ethyl>-1H-pyrrole-3-carboxamide 
• 125995-03-1 atorvastatin lactone 
• 134523-07-2 (-)-(4S)-trans-2-(4-fluorophenyl)-5-(1-methylethyl)-N,3-diphenyl-1-<(tetrahydro-4-hydroxy-2-oxo-2H-pyran-6-yl)ethyl>-1H-pyrrole-4-carboxamide 
• 777093-44-4 C₃₂H₃₁FN₂O₂ 
• 777093-50-2 C₃₂H₃₁FN₂O₂ 
• 777093-53-5 C₃₂H₃₁FN₂O₂ 
• 95061-46-4 (R)-1,1,2-triphenylethane-1,2-diol 
• 134394-96-0 *,S^*)>-5-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-3-hydroxy-1-pentanoic acid, 2-hydroxy-1,2,2-triphenylethyl ester 
• 134394-96-0 (S)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid (S)-2-hydroxy-1,2,2-triphenylethyl ester 
• 777093-10-4 5-(4-fluorophenyl)-1-(3-hydroxyhex-5-enyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide 
• 777093-40-0 C₃₂H₃₃FN₂O₂ 

Relevant articles and documents

The total synthesis of calcium atorvastatin

A practical and convergent asymmetric route to calcium atorvastatin (1) is reported. The synthesis of calcium atorvastatin (1) was performed using the remote 1,5-anti asymmetric induction in the boron-mediated aldol reaction of β-alkoxy methylketone (4) with pyrrolic aldehyde (3) as a key step. Calcium atorvastatin was obtained from aldehyde (3) after 6 steps, with a 41% overall yield.

PROCESS FOR THE PREPARATION OF ATORVASTATIN AND INTERMEDIATES

A process is provided for preparing (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, R-substituted ester 9 comprising: (a) reacting the aldehyde 1 with the enolate form of (S)-2-hydroxy-1,2,2-triphenylethyl acetate substituent in a chelating co-solvent; (b) hydrolysis of (R,S)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid, (S)-2-hydroxy-1,2,2-triphenylethyl ester (2a and 2b) using a base, preferably an alkali metal base, preferably in a solvent to form the carboxylic acid 7; (c) treating the acid 7 with a chiral base to form a salt and purifying the salt to obtain enantiomerically enriched (R)-7 chiral base salt; (d) alkylation of the (R)-7 chiral base salt or the free base derived from (R)-7, forming (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, R-substituted ester 9 and atorvastatin calcium 6, wherein R is a C1 to C6 alkyl, C6 to C9 aryl or C7 to C10 aralkyl.

Trans-6-[2-(3- or 4-Carboxamido-substituted pyrrol-1-yl)-alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis

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