188016-51-5

Basic information

• Product Name: METHYL N-(BUTOXYCARBONYL)-3-{[(5R)-3-(4-CYANOPHENYL)-4,5-DIHYDROISOXAZOL-5-YL]ACETAMIDO}-L-ALANINATE
• Synonyms: METHYL N-(BUTOXYCARBONYL)-3-{[(5R)-3-(4-CYANOPHENYL)-4,5-DIHYDROISOXAZOL-5-YL]ACETAMIDO}-L-ALANINATE
• CAS NO: 188016-51-5
• Molecular Formula: C₂₁H₂₆N₄O₆
• Molecular Weight: 0
• Mol File: 188016-51-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL N-(BUTOXYCARBONYL)-3-{[(5R)-3-(4-CYANOPHENYL)-4,5-DIHYDROISOXAZOL-5-YL]ACETAMIDO}-L-ALANINATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL N-(BUTOXYCARBONYL)-3-{[(5R)-3-(4-CYANOPHENYL)-4,5-DIHYDROISOXAZOL-5-YL]ACETAMIDO}-L-ALANINATE(188016-51-5)
• EPA Substance Registry System: METHYL N-(BUTOXYCARBONYL)-3-{[(5R)-3-(4-CYANOPHENYL)-4,5-DIHYDROISOXAZOL-5-YL]ACETAMIDO}-L-ALANINATE(188016-51-5)

Safety Data

• Hazardous Substances Data: 188016-51-5(Hazardous Substances Data)

Upstream product

• 169605-35-0 (S)-3-amino-2-butoxycarbonylamino-propionic acid methyl ester 
• 181023-08-5 (R)-2-[3-(4-cyanophenyl)-4,5-dihydroisoxazol-5-yl]acetic acid 
• 188016-53-7 N2-n-butoxycarbonyl-L-2,3-diaminopropionic acid 
• 181023-07-4 isobutyl 2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate 
• 105-07-7 4-cyanobenzaldehyde 
• 52707-54-7 4-cyanobenzaldehyde oxime 
• 213968-12-8 [3-(4-cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-thioacetic acid ethyl ester 

Relevant articles and documents

Novel chiral auxiliary for attempted resolution of key roxifiban intermediate: A simple diastereoselective coupling approach for the synthesis of roxifiban

This article describes a simple method for the synthesis of roxifiban, a potent glycoprotein GP IIb-IIIa receptor antagonist, by a diastereoselective coupling approach to give >99.9% optical purity. We have also described an attempt to resolve the key syn

Crystalline roxifiban

The potent platelet glycoprotein IIb/IIIa antagonist, roxifiban, is produced in crystalline form. Crystalline roxifiban exists in two polymorphic forms, designated Form 1 and Form 2. These polymorphic forms are characterized by x-ray powder diffraction and solid-state carbon NMR. Pharmaceutical compositions and methods for the treatment or prevention of diseases mediated by platelet aggregation are described.

The enantiospecific synthesis of an isoxazoline. A RGD mimic platelet GPIIb/IIIa antagonist

A convergent, large-scale, chiral synthesis of isoxazoline 1 has been achieved in 37% overall yield and > 99.6% optical purity, starting from L-asparagine and 4-cyanobenzaldehyde. Hofmann reaction of N(α)-n-Boc-L-asparagine with iodosobenzene diacetate provides optically pure N(α)-n-Boc-L-α,β-diaminopropionic acid (8) in 75% yield. A process of lipase resolution-base catalyzed epimerization gives the single enantiomer 5. Reaction of acid 5 with amine 9 in the presence of thionyl chloride forms the framework of 1. A Pinner reaction of intermediate 4 in methyl acetate or anisole, followed by an amidination with ammonium acetate, gives optically pure product 1.

Discovery of an orally active series of isoxazoline glycoprotein IIb/IIIa antagonists

Using isoxazoline XR299 (la) as a starting point for the design of highly potent, long-duration GPIIb/IIIa antagonists, the effect of placing lipophilic substituents at positions α and β to the carboxylate moiety was evaluated. Of the compounds studied, it was found that the n-butyl carbamate 24u1,2 exhibited superior potency and duration of ex vivo antiplatelet effects in dogs. Replacement of the benzamidin-4-yl moiety with alternative basic groups, elimination of the isoxazoline stereocenter, and reversal of the orientation of the isoxazoline ring resulted in lowered potency and/or duration of action.

The chiral specific synthesis of DMP 754, a platelet GP IIb/IIIa antagonist

An effective and chiral specific synthesis of DMP 754 (1), a non- peptide platelet GP IIb/IIIa antagonist, is reported.