51161-88-7

Basic information

• Product Name: N-Methacryloyl-L-proline
• Synonyms: N-Methacryloyl-L-proline;SJAYUJDJZUWFDO-ZETCQYMHSA-N
• CAS NO: 51161-88-7
• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.20442
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 51161-88-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-Methacryloyl-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methacryloyl-L-proline(51161-88-7)
• EPA Substance Registry System: N-Methacryloyl-L-proline(51161-88-7)

Safety Data

• Hazardous Substances Data: 51161-88-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

N-Methacryloyl-L-proline is a reactant used in the preparation of affinity ligands for the androstane receptor.

Upstream product

• 344-25-2 D-Prolin 
• 920-46-7 Methacryloyl chloride 
• 147-85-3 L-proline 
• 7732-18-5 water 

Downstream Products

• 64805-62-5 (S)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline 
• 927203-28-9 (3R,8αR)-3-(bromomethyl)-3-methyl-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 
• 106089-19-4 3(S)-(bromomethyl)-3(S)-methyl-1,4-dioxo-3,4,6,7,8,8a(S)-hexahydro-1H-pyrrolo<2,1-c><1,4>oxazine 
• 64838-55-7 (2S)-1-[(2S)-3-acetylthio-2-methylpropanoyl]pyrrolidine-2-carboxylic acid 
• 65167-28-4 (2S)-1-((2R)-3-(acetylthio)-2-methylpropanoyl)pyrrolidine-2-carboxylic acid 
• 75105-86-1 dicyclohexylamine salt of 1-[3-(4-chloro-3-sulfamoylbenzoylthio)-2(S)-methylpropionyl]-L-proline 
• 927203-28-9 3-bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 

Relevant articles and documents

Synthetic method of alpha-hydroxypropanamide derivatives with optical activity

The invention discloses a synthetic method of alpha-hydroxypropanamide derivatives with optical activity and belongs to the field of organic synthesis. Proline taken as a chiral auxiliary, as well asmethacryloyl chloride, is subjected to acylation, bromination and chiral auxiliary removal, a product and 4-cyano-3-trifluoromethylaniline are subjected to nucleophilic substitution, and 3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-trifluoromethyl)phenyl]propanamide is obtained and subjected to nucleophilic substitution with 4-cyanophenol, and the compound 3-(4-cyanophenoxy)-N-[4-cyano-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. 3-bromo-2-hydroxy-2-methyl propionic acid and 4-nitro-3-trifluoromethylaniline are subjected to aminolysis, a product is subjected to nucleophilic substitution with paracetamol, and the compound 3-(4-acetoxyphenoxy)-N-[4-nitro-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. The efficient synthetic method of the alpha-hydroxypropanamide derivatives with optical activity is provided.

SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF

This invention provides novel indole, indazole, benzimidazole, indoline, quinolone, isoquinoline, and carbazole selective androgen receptor degrader (SARD) compounds, pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, androgenic alopecia or other hyper androgenic dermal diseases, Kennedy's disease, amyotrophic lateral sclerosis (ALS), and uterine fibroids, and to methods for reducing the levels of androgen receptor-full length (AR-FL) including pathogenic and/or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.

Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries

The conjugate addition of thioacetic acid to methacrylamides with chiral C2-symmetric trans-2,5-disubstituted pyrrolidines afforded the addition products in excellent stereoselectivities (>99% de) and good yields (80-90%). The high selectivity was attributed mainly to the steric effect of the chiral auxiliaries. The cyclic nature of the chiral auxiliaries seemed also important for both the stereoselectivity and the reaction rate. Acidic hydrolysis of the adduct containing (2R,5R)-bis(methoxymethyl)pyrrolidine gave (S)-3-mercapto-2-methylpropanoic acid, a key intermediate for captopril, in 98% ee and 96% yield. The chiral auxiliary was recovered in the demethylated form of N-Boc-(2R,3R)-bis(hydroxymethyl)pyrrolidine in 90% yield.