Atazanavir sulfate CAS 229975-97-7

Introduction：Basic information about Atazanavir sulfate CAS 229975-97-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Atazanavir sulfate Basic information

• Product Name: Atazanavir sulfate
• Synonyms: N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethyl-1-oxobutyl]amino]-4-phenylbutyl]-2-[(4-phenylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamic acid methyl;BMS 232632 sulfate;BMS 232632 SULFATE;BMS-232632 SULFATE;BMS232632 SULFATE;BMS232632 sulfate;BMS-232632 sulfate;1-(4-Biphenylyl)-4(S)-hydroxy-5(S)-2,5-bis{[N-(methoxycarbonyl-)-L-tert-leucinyl]amino}-6-phenyl-2-azahexane;Aids060276;Aids-060276
• CAS: 229975-97-7
• MF: C38H54N6O11S
• MW: 802.94
• EINECS: 620-495-2
• Product Categories: Inhibitors;peptides;BMS-232632-05, Reyataz;Inhibitor;Atazanavir;Antiviral Agents;229975-97-7
• Mol File: 229975-97-7.mol

Atazanavir sulfate Chemical Properties

• Melting point: 195.0°, or acetone; mp 198-199° (dec)
• alpha: D22 -46.1° (c = 1 in 1:1 CH3OH/H2O, pH = 2.6)
• density: 1.178
• storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
• solubility: ≥28.7 mg/mL in DMSO with gentle warming; insoluble in H2O; ≥4.05 mg/mL in EtOH with gentle warming and ultrasonic
• form: Powder
• color: White to light yellow
• Optical Rotation: [α]/D -40 to -50°, c =1 in methanol: water (1:1)
• Water Solubility: H2O: 2mg/mL, clear
• InChIKey: DQSGVVGOPRWTKI-ZTSWSJPKNA-N
• SMILES: S(O)(O)(=O)=O.N(NC(=O)[C@H](C(C)(C)C)NC(=O)OC)(C[C@H](O)[C@@H](NC(=O)[C@H](C(C)(C)C)NC(=O)OC)CC1C=CC=CC=1)CC1C=CC(C2N=CC=CC=2)=CC=1 |&1:9,20,22,26,r|

Safety Information

• Safety Statements: 24/25
• WGK Germany: WGK 3
• HS Code: 29333990
• Storage Class: 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
• Hazard Classifications: Eye Dam. 1 STOT RE 1

Atazanavir sulfate Usage And Synthesis

Description

Atazanavir (BMS-232632, III), an azapeptide HIVprotease inhibitor, has been developed and launched byBristol-Myers Squibb (BMS), under worldwide license fromNovartis, for the treatment of HIV infection. Atazanavirwas launched in the US as Reyataz™ in July 2003.

Chemical Properties

Off-White Solid

Uses

Atazanavir is a novel azapeptide HIV protease inhibitor (PI). Antiviral.

Uses

Atazanavir is a HIV protease inhibitor with Ki of 2.66 nM

Uses

Atazanavir Sulfate is an intermediate of Atazanavir(A790051) which is a novel azapeptide HIV protease Inhbitor. Antiviral.

Brand name

Reyataz(Bristol-Myers Squibb).

Synthesis

Thesynthesis of atazanavir (III) appeared in several reports. The synthetic route depicted in the scheme was one ofthe best routes which was suitable for large scale production. The commercially available chiral diol 25 wasconverted to its silyl mesylate 26 in one pot via selectivesilylation and subsequent mesylation. This oily intermediate26 was carried into the next step without further purification.The desilylation of 26 was achieved by using inexpensiveammonium fluoride. The resulting solid product 27 wasreadily isolated and further purified through recrystallizationfrom IPA/H2O in 80% yield. The epoxide formation from27 was affected by KO^tBu in THF/IPA to provide enantiomerically pure epoxide 28 in 88% yield. Suzukicoupling of boronic acid 29 with bromopyridine (30)provided pyridyl benzaldehyde 31 in 80% yield aftercrystallization. The subsequent condensation of aldehyde 31with t-butylcarbamate was carried out by refluxing intoluene/IPA and Shiff base 32 was collected by filtrationupon cooling. Reduction of hydrazone 32 to hydrazine 33was accomplished by employing a catalytic phase-transferhydrogenation protocol (Pd/C, HCOONa) to furnishhydrazine 33 in 78% yield after crystallization. Coupling ofthe hydrazinocarbamate 33 with epoxide 28 was performedin refluxing IPA, followed by the addition of water toprecipitate the crude product. Subsequent recrystallizationfrom MeCN/H2O furnished 34 in 85% yield. Treatment of34 with concentrated HCl in THF at 50oC removed the twoBoc groups in 34 to give the product as an oil, which wasthen dissolved in a mixture of DCM/DIPEA and slowlytransferred into a premixed solution of N-methoxycarbonyl-L-tert-leucine (35), HOBT, and WSC in DCM. Afterremoval of the solvent the crude product was crystallizedfrom IPA/EtOH to furnish the freebase 36 in 82% yield. Thesulfate III was obtained by stirring the free base 36 withconcentrated H2SO4 in EtOH at ambient temperature. Directcrystallization by addition of n-heptane provided the sulfatesalt III as an easily filterable solid in 85% yield.