240821-65-2

Basic information

• Product Name: (4S)-3-[(2S)-2-(1-methylethyl)-1-oxopent-4-en-1-yl]-4-(phenylmethyl)oxazolidin-2-one
• Synonyms: (4S)-3-[(2S)-2-(1-methylethyl)-1-oxopent-4-en-1-yl]-4-(phenylmethyl)oxazolidin-2-one
• CAS NO: 240821-65-2
• Molecular Weight: 301.386
• Mol File: 240821-65-2.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (4S)-3-[(2S)-2-(1-methylethyl)-1-oxopent-4-en-1-yl]-4-(phenylmethyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-3-[(2S)-2-(1-methylethyl)-1-oxopent-4-en-1-yl]-4-(phenylmethyl)oxazolidin-2-one(240821-65-2)
• EPA Substance Registry System: (4S)-3-[(2S)-2-(1-methylethyl)-1-oxopent-4-en-1-yl]-4-(phenylmethyl)oxazolidin-2-one(240821-65-2)

Safety Data

• Hazardous Substances Data: 240821-65-2(Hazardous Substances Data)

Upstream product

• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 145589-03-3 (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 
• 106-95-6 allyl bromide 
• 556-56-9 allyl iodid 

Downstream Products

• 1310055-48-1 (Z)-(4S)-4-benzyl-3-[(2S,7S)-7-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-2-isopropyl-8-methylnon-4-enoyl]-1,3-oxazolidin-2-one 
• 1413429-42-1 (3S,5S)-dihydro-5-{(1S,3S)-1-hydroxy-3-[4-methoxy-3-(3-methoxypropoxy)benzoyl]-4-methylpentyl}-3-(1-methylethyl)furan-2(3H)-one 
• 393108-57-1 (3S,5S)-5-{(1R,3S)-1-bromo-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-dihydro-3-(1-methylethyl)furan-2(3H)-one 
• 325154-26-5 (2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-N,N,8-trimethylnon-4-enamide 
• 935534-00-2 (S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanal 
• 1381862-11-8 (R)-1-(3-methoxypropoxy)-2-methoxy-5-(2-isopropyl-4-pentenyl)benzene 
• 1381862-10-7 C₁₉H₂₈O₄ 
• 1322077-34-8 C₁₇H₂₁NO₄ 

Relevant articles and documents

Alkene chemoselectivity in ring-closing metathesis: A formal synthesis of (-)-periplanone-B

A synthesis of the (-)-dienone 1 (R = Pr(i)) via ring-closing alkene metathesis to give the substituted dihydropyran 13 in the presence of alkenyl iodide functionality is described.

The development of a complementary pathway for the synthesis of aliskiren

The synthesis of aliskiren (1), a recently marketed drug for the treatment of hypertension, is presented. The focus of our synthetic effort is to develop an efficient pathway for the synthesis of (2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy) benzyl)-N,N,8-trimethylnon-4-enamide (2a), which has been used as the advanced intermediate toward aliskiren. After an extensive investigation of three different strategies designed to construct the E-olefin functionality in 2a by employing the olefin cross-metathesis, Horner-Wadsworth-Emmons (HWE), and Julia-type olefinations, we have established a new protocol for the synthesis of 2a with a substantially improved overall efficiency in terms of the yield (ca. 33%), and diastereo- and E/Z-selectivity. The key transformations were the Evans chiral auxiliary-aided asymmetric allylation for the synthesis of the appropriate chiral intermediates in excellent enantiomeric purity of higher than 97% ee and a modified Julia-Kocienski olefination for the highly selective construction of E-2a with up to 13.6:1 E/Z ratio from the chiral intermediates. Consequently, the results provide an appealing option for the synthesis of aliskiren. This journal is

A new synthesis of the orally active renin inhibitor aliskiren

A convergent synthesis of the orally active renin inhibitor aliskiren (1) is described. The synthesis was accomplished in 12 steps starting from the known chloride 2. The key step involves the Curtius rearrangement of the advanced intermediate 15, which provides lactone/carbamate 17 containing the correct stereochemistry and all of the functionality required for the preparation of the drug substance.

Process and intermediates for the preparation of aliskiren

The present invention relates to a process and intermediates for the manufacture of aliskiren or pharmaceutically acceptable salts thereof.