102089-75-8

Basic information

• Product Name: N-[(1R)-2-[(Methylsulfonyl)oxy]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester
• Synonyms: N-[(1R)-2-[(Methylsulfonyl)oxy]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester
• CAS NO: 102089-75-8
• Molecular Formula: C₁₄H₂₁NO₅S
• Molecular Weight: 315.38524
• Mol File: 102089-75-8.mol

Chemical Properties

• Melting Point: 112-114℃
• Boiling Point: 497.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.204±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly, Sonicated), Dichloromethane; Ethyl Acetate; Methanol (Slig
• PKA: 11.11±0.46(Predicted)
• CAS DataBase Reference: N-[(1R)-2-[(Methylsulfonyl)oxy]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1R)-2-[(Methylsulfonyl)oxy]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester(102089-75-8)
• EPA Substance Registry System: N-[(1R)-2-[(Methylsulfonyl)oxy]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester(102089-75-8)

Safety Data

• Hazardous Substances Data: 102089-75-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-[(1R)-2-[(Methylsulfonyl)oxy]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester is used as a key intermediate in the synthesis of Elagolix-d6 Sodium Salt (E501016), a labelled analogue of Elagolix Sodium Salt (E501018). Elagolix Sodium Salt is a novel uracil phenylethylamine that acts as a potent human gonadotropin-releasing hormone receptor (hGnRH-R) antagonist. This antagonistic action makes it a potential candidate for treating various hormonal disorders and conditions related to the gonadotropin-releasing hormone receptor.
In the synthesis process, N-[(1R)-2-[(Methylsulfonyl)oxy]-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester contributes to the formation of the final product, Elagolix-d6 Sodium Salt, which can be used for research purposes, such as studying the mechanism of action of hGnRH-R antagonists and their potential therapeutic applications. This intermediate is essential for the development of new drugs and therapies that target the hormonal system and can lead to improved treatment options for patients suffering from related conditions.

Upstream product

• 67341-01-9 (R)-N-(tert-butoxycarbonyl)phenylglycinol 
• 124-63-0 methanesulfonyl chloride 
• 56613-80-0 D-2-phenylglycinol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 102089-74-7 tert-butyl 2-hydroxy-1-phenylethylcarbamate 
• 7143-01-3 Methanesulfonic anhydride 
• 141190-94-5 (R)-N-(tert-butoxycarbonyl)phenylglycine methyl ester 

Downstream Products

• 155392-49-7 (R)-N-(tert-butoxycarbonyl)-1-phenyl-2-piperidinylethylamine 
• 1027920-03-1 ((R)-1-Phenyl-2-thiomorpholin-4-yl-ethyl)-carbamic acid tert-butyl ester 
• 110143-60-7 N-(benzyloxycarbonyl)-S-<(R)-2-<(tert-butoxycarbonyl)amino>-2-phenylethyl>-L-cysteine diphenylmethyl ester 
• 126301-24-4 (R)-2-amino-2-phenylethyl methanesulphonate hydrochloride 
• 134557-76-9 (R)-(-)-1-<(butoxycarbonyl)amino>-1-phenylethyl azide 
• 126568-44-3 (S)-3-(N-tert-butoxycarbonylamino)-3-phenylpropanenitrile 
• 224633-13-0 (R)-tert-butyl (2-(1,3-dioxoisoindolin-2-yl)-1-phenylethyl)carbamate 
• 224633-14-1 (R)-N-(tert-butoxycarbonyl)-α-(dimethylaminomethyl)benzylamine 
• 860304-34-3 [2-(3-bromo-benzoylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 174636-94-3 (R)-N²,N²-dimethyl-1-phenyl-1,2-ethanediamine 
• 174636-89-6 (R)-2-(2-amino-2-phenylethyl)isoindoline-1,3-dione 
• 830346-44-6 3-[2(R)-{tert-butoxycarbonylamino}-2-phenylethyl]-5-(2-chloro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)-benzyl]pyrimidine-2,4-(1H,3H)-dione 
• 289051-61-2 (-)-(2R)-[(1',1'-dimethylethoxycarbonyl)amino]-2-phenylethanethiol 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 

Relevant articles and documents

Discovery and Optimization of Phosphopantetheine Adenylyltransferase Inhibitors with Gram-Negative Antibacterial Activity

In the preceding manuscript [Moreau et al. 2018, 10.1021/acs.jmedchem.7b01691] we described a successful fragment-based lead discovery (FBLD) strategy for discovery of bacterial phosphopantetheine adenylyltransferase inhibitors (PPAT, CoaD). Following several rounds of optimization two promising lead compounds were identified: triazolopyrimidinone 3 and 4-azabenzimidazole 4. Here we disclose our efforts to further optimize these two leads for on-target potency and Gram-negative cellular activity. Enabled by a robust X-ray crystallography system, our structure-based inhibitor design approach delivered compounds with biochemical potencies 4-5 orders of magnitude greater than their respective fragment starting points. Additional optimization was guided by observations on bacterial permeability and physicochemical properties, which ultimately led to the identification of PPAT inhibitors with cellular activity against wild-type E. coli.

Electrochemical Deoxygenative Thiolation of Preactivated Alcohols and Ketones

This work describes an electrochemically promoted nickel-catalyzed deoxygenative thiolation of alcohols and ketones under mild conditions. Excellent substrate tolerance and good chemical yields can be achieved by graphene/nickel foam electrodes in an undivided cell. Further study to gain mechanistic insight into this electrochemical cross-coupling has been carried out.

AN IMPROVED PROCESS FOR THE PREPARATION OF ELAGOLIX SODIUM

An improved process for the preparation of Elagolix Sodium having the structural formula (I). The present invention relates to highly pure compound of formula (VI) as a solid which is useful in the preparation of Elagolix sodium. The present invention pro

AN IMPROVED PROCESS FOR THE PREPARATION OF 4-({(1 R)-2-[5-(2-FLUORO-3METHOXYPHENYL)-3-{[2-FLUORO-6-(TRIFLUORO METHYL) PHENYL]METHYL}-4-METHYL-2,6-DIOXO-3,6DIHYDROPYRIMIDIN-1(2 H)-YL]-1-PHENYLETHYL}AMINO)BUTANOIC ACID OR ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to an improved process for the preparation of 4- ({(1R) -2- [5- (2-fluoro- 3- methoxy phenyl) – 3 - {[ 2-fluoro- 6-(trifluoro methyl) phenyl] methyl} -4-methyl- 2,6-dioxo- 3,6-dihydropyrimidin-1(2H)-yl]-1-phenylethyl}amino) butanoic acid of formula (I) or its pharmaceutically acceptable salts. The compound of formula (I) is represented by the following structural formula.

Elagolix Sodium Compositions and Processes

The present invention relates to compositions of elagolix sodium, and process and intermediates for the preparation thereof.

Late-Stage Isotopic Carbon Labeling of Pharmaceutically Relevant Cyclic Ureas Directly from CO2

A robust, click-chemistry-inspired procedure for radiolabeling of cyclic ureas was developed. This protocol, suitable for all carbon isotopes (11C, 13C, 14C), is based on the direct functionalization of carbon dioxide: the universal building block for carbon radiolabeling. The strategy is operationally simple and reproducible in different radiochemistry centers, exhibits remarkably wide substrate scope with short reaction times, and demonstrates superior reactivity as compared to previously reported systems. With this procedure, a variety of pharmaceuticals and an unprotected peptide were labeled with high radiochemical efficiency.

Synthesis and biological evaluation of 3-(2-aminoethyl) uracil derivatives as gonadotropin-releasing hormone (GnRH) receptor antagonists

We investigated a series of uracil analogues by introducing various substituents on the phenyl ring of the N-3 aminoethyl side chain and evaluated their antagonistic activity against human gonadotropin-releasing hormone (GnRH) receptors. Analogues with su

Synthesis, SAR and evaluation of [1,4′]-bipiperidinyl-4-yl-imidazolidin-2-one derivatives as novel CCR5 antagonists

Elaboration of our previously disclosed spiropiperidine template led to the development of a series of novel CCR5 antagonists. Results of SAR exploration and preliminary lead characterization are described.

PROCESSES FOR THE PREPARATION OF URACIL DERIVATIVES

The present invention relates to processes and intermediates for preparing Gonadotropin-Releasing Hormone (GnRH) receptor antagonists of structure (VI); and stereoisomers and pharmaceutically acceptable salts thereof.

Configurational flexibility of epimeric β-aminothioether-chelated ruthenium(II) η6-arene complex salts

Five chiral β-aminothioethers were obtained via different routes orientated on literature protocols. Three of these β-aminothioethers were reacted with two di-μ-chloro-bis{chloro[η6-arene]- ruthenium(II)} derivatives, resulting in the title complex salts. The complex cations exhibit three stereocenters, viz. ruthenium and sulfur atoms and the chiral benzylic carbon atom of the chelate ligand backbone. Both, ruthenium and sulfur stereocenters epimerize into a mixture of four NMR distinguishable diastereomers in equilibrium, but the designed chiral benzylic carbon atom is stable under all conditions applied so far. The relative diastereomer concentrations in solution depend mainly on the spatial requirements of the η6-arene ligand rather than on the thioether moiety. Diastereomer ratios and the absolute configurations in solution were studied by NMR and CD spectroscopy. The spectroscopic results fit to the absolute X-ray crystal structure parameters determined for the diastereomers present in the crystalline state.