(alphaR)-alpha-Hydroxy-N-[2-(4-nitrophenyl)ethyl]benzeneacetamide

Base Information

• Chemical Name: (alphaR)-alpha-Hydroxy-N-[2-(4-nitrophenyl)ethyl]benzeneacetamide
• CAS No.: 521284-19-5
• Molecular Formula: C16H16N2O4
• Molecular Weight: 300.314
• Mol file: 521284-19-5.mol

Synonyms:(2R)-2-Hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide; Mirabegron Intermediate 1; (alphaR)-alpha-Hydroxy-N-[2-(4-nitrophenyl)ethyl]benzeneacetamide; (R)-2-hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide

Chemical Property of (alphaR)-alpha-Hydroxy-N-[2-(4-nitrophenyl)ethyl]benzeneacetamide

Chemical Property:

• Boiling Point: 584.8±50.0 °C(Predicted)
• PKA: 12.50±0.20(Predicted)
• PSA: 98.64000
• Density: 1.294
• LogP: 3.35060
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%, ^*data from raw suppliers

(2R)-2-Hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (ALPHAR)-ALPHA-hydroxy-N-[2-(4-nitrophenyl)ethyl]phenylacetamide is an organic amide, which can be used as a pharmaceutical intermediate. (2R)-2-Hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide is an intermediate used to prepare (aminothiazolyl)acetanilide derivatives via coupling reactions for treatment of diabetes.

Technology Process of (alphaR)-alpha-Hydroxy-N-[2-(4-nitrophenyl)ethyl]benzeneacetamide

There total 19 articles about (alphaR)-alpha-Hydroxy-N-[2-(4-nitrophenyl)ethyl]benzeneacetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(R)-2-((4-nitrophenethyl)amino)-2-oxo-1-phenylethyl acetate → (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide (521284-19-5)

Guidance literature:

With sodium hydroxide; In ethanol; at 30 ℃; for 3h; pH=12; Concentration; Solvent; pH-value; Reagent/catalyst; Temperature;

Reference yield: 95.0%

(R)-2-((4-nitrophenethyl)amino)-2-oxo-1-phenylethyl benzoate → (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide (521284-19-5)

Guidance literature:

With potassium hydroxide; In acetonitrile; at 30 ℃; for 4h; pH=11; Temperature; Reagent/catalyst;

Reference yield: 92.3%

2-(p-nitrophenyl)ethylamine (24954-67-4) + (R)-Mandelic Acid (611-71-2) → (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide (521284-19-5)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; at 150 ℃; for 9h; Temperature; Inert atmosphere;

upstream raw materials:

(R)-Mandelic Acid

2-(4-nitrophenyl)ethylamine monohydrochloride

2-(p-nitrophenyl)ethylamine

(R)-Mandelsaeure, Natrium-Salz

Downstream raw materials:

(R)-2-(4-nitrophenylethylamino)-1-phenylethan-1-ol hydrochloride

(R)-2-[ [2-(4-aminophenyl)ethyl]-amino]-1-phenylethanol monohydrochloride

(R)-(4-aminophenylethyl)(2-hydroxy-2-phenylethyl)carbamic acid tert-butyl ester

((2R)-2-hydroxy-2-phenylethyl)-[2-(4-nitrophenyl)ethyl]carbamic acid tert-butyl ester

Refernces

• 1、 Bangal, Mukund N.,Deshmukh, Dattatray G.,Kalawade, Kaustubh A.,Mathad, Vijayavitthal T.. "Systematic Investigation into the Formation of Significant Amounts of Unknown Impurity during Scale-up of NaBH4-I2 Mediated Reduction of Nitro-Amide Intermediate of Mirabegron No.". . p. 286 - 293. Retrieved 2020/03/10.
• 2、 -. "Amide substituted pyrrolidine amide derivatives and use thereof (by machine translation)". Paragraph 0233; 0235; 0236. . Retrieved 2019/06/07.