181023-07-4

Basic information

• Product Name: ISOBUTYL-3-(4-CYANOPHENYL)-4,5-DIHYDRO-5-ISOXAZOLE ACETATE
• Synonyms: ISOBUTYL-3-(4-CYANOPHENYL)-4,5-DIHYDRO-5-ISOXAZOLE ACETATE
• CAS NO: 181023-07-4
• Molecular Formula: C₁₆H₁₈N₂O₃
• Molecular Weight: 286.33
• Mol File: 181023-07-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ISOBUTYL-3-(4-CYANOPHENYL)-4,5-DIHYDRO-5-ISOXAZOLE ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOBUTYL-3-(4-CYANOPHENYL)-4,5-DIHYDRO-5-ISOXAZOLE ACETATE(181023-07-4)
• EPA Substance Registry System: ISOBUTYL-3-(4-CYANOPHENYL)-4,5-DIHYDRO-5-ISOXAZOLE ACETATE(181023-07-4)

Safety Data

• Hazardous Substances Data: 181023-07-4(Hazardous Substances Data)

Upstream product

• 24342-03-8 isobutyl vinylacetate 
• 10447-96-8 4-cyano-benzonitrile N-oxide 
• 105-07-7 4-cyanobenzaldehyde 
• 181023-09-6 isobutyl (S)-2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate 
• 52707-54-7 4-cyanobenzaldehyde oxime 

Downstream Products

• 213968-12-8 [3-(4-cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-thioacetic acid ethyl ester 
• 181023-08-5 (R)-2-[3-(4-cyanophenyl)-4,5-dihydroisoxazol-5-yl]acetic acid 
• 181023-09-6 isobutyl (S)-2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate 
• 188016-51-5 (2S)-2-butoxycarbonylamino-3-[2-[(5R)-3-(4-cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetylamino]-propionic acid methyl ester 

Relevant articles and documents

Efficient Preparation of a Key Intermediate in the Synthesis of Roxifiban by Enzymatic Dynamic Kinetic Resolution on Large Scale

Additional information is presented for the transformation of a kinetic resolution into a dynamic kinetic resolution of the isobutyl ester 5b to form the acid 2 in high yield and ee via the intermediacy of a thioester 6c, (Pesti, J. A.; Yin, J.; Zhang, L.-H; Anzalone, L. J. Am. Chem. Soc. 2001, 123, 11075-11076.). The development of optimized reaction conditions for the preparation of 6c, its dynamic kinetic resolution to 2, and the scale-up of both reactions into a pilot plant 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.

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.