923590-37-8

Basic information

• Product Name: (1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone
• Synonyms: MK 7009;Vaniprevir;MK 7009/Vaniprevir;Vaniprevir(MK-7009);(1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone
• CAS NO: 923590-37-8
• Molecular Formula: C38H55N5O9S
• Molecular Weight: 757.94
• Product Categories: API
• Mol File: 923590-37-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 175-177 °C
• Appearance: /
• Density: 1.33
• PKA: 4.58±0.40(Predicted)
• CAS DataBase Reference: (1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone(923590-37-8)
• EPA Substance Registry System: (1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone(923590-37-8)

Safety Data

• Hazardous Substances Data: 923590-37-8(Hazardous Substances Data)

Usage

Description

(1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers at the 1R and 2R positions, as well as its various functional groups, including carboxylic acids, amide bonds, and lactone rings. (1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone has potential applications in various fields due to its unique properties and reactivity.

Uses

Used in Pharmaceutical Industry:
(1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone is used as a pharmaceutical agent for the treatment of various diseases. Its unique molecular structure allows it to interact with specific biological targets, making it a promising candidate for drug development.
Used in Chemical Research:
(1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone is also used in chemical research as a model compound to study the synthesis and reactivity of complex organic molecules. Its chiral centers and various functional groups provide opportunities for exploring new synthetic routes and understanding the relationship between molecular structure and reactivity.
Used in Material Science:
(1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone can be used in material science to develop new materials with unique properties. Its ability to form hydrogen bonds and interact with other molecules makes it a potential candidate for the development of self-assembling materials, sensors, and other advanced materials.

Synthesis

Beginning with commercial bis-benzylbromide 311, subjection to benzylamine under basic conditions followed by acidification afford the isoindoline as the toluene sulfonic acid salt 312. This salt was then freebased and acylative removal of the benzyl protecting group took place through the use of acetyl chloride. Hydrochloric acid in refluxing methanol removed the acetamide to liberate indoline 313, which was isolated as the HCl salt. Next, exposure of 313 to alcohol 314 in the presence of CDI and warm DMF gave rise to carbamate 315. This was followed by Heck installation of n-hexenyl fragment 316 and subsequent hydrogenation of the olefin with concomitant removal of the benzoyl carbamate protecting group delivered macrocycle precursor 317. Next, an intramolecular lactamization reaction furnished the macrocyclic system and this was followed by saponification of the prolinate ester to give 318. This acid was then coupled with cyclopropylamine 319 under standard coupling conditions to furnish vaniprevir in 87% yield.The preparation of hexenyl fragment 316 started with the lithiation of commercially available ethyl isobutyrate (320) and alkylative quench with 1-bromo-4-butene to provide hexenyl ester 321. Next, DIBAL reduction followed by CDI-mediated carbamate formation with L-t-leucine and subsequent treatment with dicyclohexylamine (DCHA) furnished the key hexenyl fragment 316. The assembly of cyclopropylamine 319 stems from cyclopropyl fragment 34, whose synthesis was described in Scheme 5. Hydrogenation of this system to saturate the double bond was followed by treatment with toluenesulfonic acid to remove the Boc group, furnishing the tosylate salt in good yield for the two step sequence.