153294-00-9

Basic information

• Product Name: (R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester
• Synonyms: methyl (R)-3-chloromandelate;(R)-(3-Chloro-phenyl)-hydroxy-acetic acid methyl ester;methyl (R)-2-(3-chlorophenyl)-2-hydroxyacetate;(R)-(-)-3-chloromandelic acid methyl ester;(R)-methyl 2-(3-chlorophenyl)-2-hydroxyacetate;(R)-methyl 3-chloromandelate;(R)-(-)-methyl 2-(3-chlorophenyl)-2-hydroxyacetate
• CAS NO: 153294-00-9
• Molecular Formula: C9H9ClO3
• Molecular Weight: 200.622
• Mol File: 153294-00-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester(153294-00-9)
• EPA Substance Registry System: (R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester(153294-00-9)

Safety Data

• Hazardous Substances Data: 153294-00-9(Hazardous Substances Data)

Usage

Description

(R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester, also known as Methyl (R)-3-Chloromandelate, is an organic compound that serves as an intermediate in the synthesis of Solabegron Hydrochloride (S676510). It is characterized by its chlorophenyl and hydroxyacetic acid ethyl ester functional groups, which contribute to its chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
(R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester is used as an intermediate in the synthesis of Solabegron Hydrochloride for the treatment of irritable bowel syndrome. Solabegron Hydrochloride is a selective β3-adrenergic receptor agonist that also produces Somatostatin (S676750), making it a valuable compound in the development of medications for gastrointestinal disorders.
Additionally, as an intermediate, (R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester may have potential applications in the synthesis of other related compounds with therapeutic properties, further expanding its utility in the pharmaceutical industry.

Upstream product

• 26767-07-7 2-(3-chlorophenyl)-2-oxoacetic acid 
• 99-02-5 3'-Chloroacetophenone 
• 16273-37-3 3-chloromandelic acid 
• 74-88-4 methyl iodide 
• 264882-01-1 methyl 3-chlorophenyldiazoacetate 
• 16273-37-3 (R)-3-chloromandelic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 
• 122047-10-3 (R)-(+)-2-hydroxy-2-(3-chlorophenyl)acetonitrile 
• 74-89-5 methylamine 
• 18166-02-4 N-trimethylsilylmethylamine 
• 587-04-2 m-Chlorobenzaldehyde 
• 108-05-4 vinyl acetate 
• 13305-18-5 (3-chlorophenyl)hydroxyacetic acid methyl ester 

Downstream Products

• 153294-01-0 methyl (2R)-{[tert-butyl(dimethyl)silyl]oxy}(3-chlorophenyl)ethanoate 
• 153294-02-1 (R)-2-(tert-butyldimethylsilyloxy)-2-(3-chlorophenyl)acetaldehyde 
• 174891-03-3 1,1-dimethylethyl ((2R)-2-(3-chlorophenyl)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)[(1R)-1-methyl-2-oxoethyl]carbamate 
• 174891-00-0 methyl (2R)-2-{(tert-butoxycarbonyl)[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl]amino}propanoate 
• 402508-91-2 tert-butyl (1R)-2-anilino-1-methylethyl-[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl]carbamate 
• 402508-95-6 tert-butyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl[(1R)-1-methyl-2-(4-{[(methylsulfonyl)amino]methyl}anilino)ethyl]carbamate 
• 402508-99-0 tert-butyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl[(1R)-1-methyl-2-(4-{2-[(methylsulfonyl)amino]-2-oxoethyl}anilino)ethyl]carbamate 
• 402508-97-8 tert-butyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl-((1R)-1-methyl-2-{4-[2-oxo-(1,3-thiazol-2-ylamino)ethyl]anilino}ethyl)carbamate 
• 402509-08-4 tert-butyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl[(1R)-1-methyl-2-(4-{2-[(4-methylbenzyl)amino]-2-oxoethyl}anilino)ethyl]carbamate 
• 402509-10-8 tert-butyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl{(1R)-1-methyl-2-[4-(2-{[(4-methylphenyl)sulfonyl]amino}ethyl)anilino]ethyl}carbamate 
• 1028300-56-2 C₃₆H₅₁ClN₄O₆SSi 
• 343239-79-2 (R)-2-(tetrahydro-[2H]-pyran-2-yloxy)-2-(3-chlorophenyl)acetic acid methylester 
• 859931-64-9 (R)-3-chloromandelamide 

Relevant articles and documents

The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation

A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX?Ru) catalyzed asymmetric hydrogenation of α-aryl keto acids has been successfully developed, affording the corresponding chiral α-aryl α-hydroxy carboxylic acids in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 5000 S/C) and the resulting products can be transformed to several chiral building blocks, biologically active compounds and chiral drugs. (Figure presented.).

Batch and Continuous-Flow One-Pot Processes using Amine Diazotization to Produce Silylated Diazo Reagents

A novel synthesis of trimethylsilyldiazomethane (TMSCHN2) by diazotization of trimethylsilylmethylamine (TMSCH2NH2) is reported using batch and continuous flow synthesis. The latter affords a daily production of 275 g (2.4 mol) of TMSCHN2. Other silylated methylamines were also successfully reacted under the developed reaction conditions to furnish various silicon-bearing diazomethane reagents. The applicability of the process is highlighted by disclosure of batch and continuous flow one-pot esterification and 1,3-dipolar cycloaddition processes. Furthermore, the high-yielding esterification of carboxylic acids with silylated and substituted methylamines in continuous flow is disclosed. Finally, work-up and purification procedures are reported for the preparation of a 2-MeTHF solution of TMSCHN2, which can be used in rhodium-catalyzed methylenation and homologation reactions.

HETEROCYCLIC COMPOUNDS AS MDM2 INHIBITORS FOR THE TREATMENT OF CANCER

The present invention provides MDM2 inhibitor compounds of Formula I or II, or the pharmaceutically acceptable salts thereof, wherein the variables are defined above, which compounds are useful as therapeutic agents, particularly for the treatment of cancers. The present invention also relates to pharmaceutical compositions that contain an MDM2 inhibitor.