134394-98-2

Basic information

• Product Name: 1,1-dimethylethyl (R)-7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate
• Synonyms: 1,1-dimethylethyl (R)-7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate
• CAS NO: 134394-98-2
• Molecular Weight: 612.741
• Mol File: 134394-98-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,1-dimethylethyl (R)-7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-dimethylethyl (R)-7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate(134394-98-2)
• EPA Substance Registry System: 1,1-dimethylethyl (R)-7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate(134394-98-2)

Safety Data

• Hazardous Substances Data: 134394-98-2(Hazardous Substances Data)

Usage

Description

1,1-dimethylethyl (R)-7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate is a complex organic compound with a unique molecular structure. It is a derivative of Atorvastatin, a selective and competitive HMG-CoA reductase inhibitor, and is protected by a Boc group, which makes it a potential precursor in the synthesis of Atorvastatin and its analogs.

Uses

Used in Pharmaceutical Industry:
1,1-dimethylethyl (R)-7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate is used as an intermediate in the synthesis of Atorvastatin and its analogs for the treatment of hypercholesterolemia. It helps in lowering elevated LDL-cholesterol and triglycerides levels in patients, thus reducing the risk of cardiovascular diseases.
Used in Drug Development:
1,1-dimethylethyl (R)-7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate is used as a starting material for the development of new drugs with improved pharmacological properties. Its unique structure allows for the exploration of novel therapeutic agents with enhanced efficacy and selectivity.
Used in Research and Development:
1,1-dimethylethyl (R)-7-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-5-hydroxy-3-oxo-1-heptanoate is used in research and development for the study of its chemical properties, reactivity, and potential applications in various fields, including material science, pharmaceuticals, and agrochemicals.

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 134394-97-1 methyl (R)-(+)-5-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-3-hydroxy-1-pentanoate 
• 864408-78-6 (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid 
• 40052-13-9 mono-tert-butyl malonate 
• 887324-52-9 Atorvastatin 
• 104197-11-7 magnesium salt of tert-butyl hydrogen malonate 
• 1207973-75-8 lithium tert-butyl acetate 
• 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 
• 143952-58-3 ethyl 3-(4-cyanophenyl)propynoate 

Downstream Products

• 134523-03-8 lipitor 
• 125995-03-1 atorvastatin lactone 

Relevant articles and documents

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.

AN IMPROVED PREPARATION OF ATORVASTATIN

A process for preparing (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-l-heptanoic acid, tert-butylester comprising: (a) reduction of 5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-l-yl]-3-oxo-l-pentanoic acid, (R)-2-hydroxy-1,2,2-triphenylethyl ester; (b) hydrolysis of (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-l-pentanoic acid, (R)-2-hydroxy-1,2,2-triphenylethyl ester using an alkali base in a solvent to form the acid; (c) alkylation of the acid forming (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1 H-pyrrol-1-yl]-5-hydroxy-3-oxo- l -heptanoic acid, tert-butylester.