70110-25-7

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-Chloropropionyl chloride is used as a key intermediate for the synthesis of various pharmaceuticals. Its reactivity and functional group compatibility make it suitable for the development of new drugs and the improvement of existing ones. It plays a critical role in the production of medications that address a wide range of health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-2-Chloropropionyl chloride is utilized as an intermediate in the creation of pesticides and other crop protection agents. Its involvement in the synthesis of these products contributes to the development of more effective and targeted solutions for agricultural challenges.
Used in Synthesis of Fine Chemicals:
(R)-2-Chloropropionyl chloride is used as a reagent in the synthesis of fine chemicals, which are high-purity chemicals used in various applications, including research, diagnostics, and specialty manufacturing. Its ability to participate in a variety of chemical reactions makes it a valuable asset in the production of these high-quality compounds.
Used in Production of Pharmaceutical Intermediates:
As a precursor in the production of pharmaceutical intermediates, (R)-2-Chloropropionyl chloride is instrumental in the development of the building blocks for new pharmaceuticals. These intermediates are essential for the synthesis of active pharmaceutical ingredients, which are the key components of medications.
It is important to handle (R)-2-Chloropropionyl chloride with care due to its potential hazards if not used properly, ensuring safety in the chemical industry and the integrity of the products it helps to create.

Upstream product

• 10326-41-7 D-Lactic acid 
• 7474-05-7 (R)-2-chloropropionic acid 
• 83261-13-6 (2S)-2-(4-toluenesulfonyloxy)propionyl chloride 
• 67-64-1 acetone 
• 87337-51-7 (+)-2(S)-fluoropropionyl chloride 

Downstream Products

• 113509-61-8 N-((R)-2-chloro-propionyl)-L-phenylalanine 
• 85038-45-5 N-((R)-2-chloro-propionyl)-glycine 
• 85277-56-1 (R)-2-chloro-1-(4'-isobutylphenyl)propan-1-one 
• 81112-08-5 N-[4-((S)-2-Chloro-propionyl)-phenyl]-acetamide 
• 132298-10-3 N-[4-((R)-2-Chloro-propionyl)-phenyl]-acetamide 
• 159141-33-0 2-chloropropionyl-L-glutamine 

Relevant academic research and scientific papers

Preparation method of D-2-chloropropionyl chloride and D-2-chloropropionyl chloride

The invention is applicable to the technical field of synthesis of medical intermediates, and provides a preparation method of D-2-chloropropionyl chloride and D-2-chloropropionyl chloride, the preparation method comprises the following steps: adding L-ethyl lactate and a catalyst into a reaction vessel, dropwisely adding thionyl chloride at -10-10 DEG C, heating to 65-70 DEG C, and carrying out heat preservation reaction; after the reaction is finished, cooling to 10-30 DEG C, and carrying out reduced pressure concentration and other treatment to obtain ethyl D-2-chloropropionate; adding resin, anhydrous formic acid and water, heating to 70-100 DEG C, and reacting for 2-5 hours; after the reaction is finished, cooling to 10-30 DEG C, filtering, and distilling to obtain D-2-chloropropionicacid; and dropwise adding thionyl chloride at 0-5 DEG C, heating to 45-65 DEG C, carrying out heat preservation reaction, and carrying out vacuum concentration and distillation treatment to obtain the product. The method realizes 10kg-grade large-scale production of D-2-chloropropionyl chloride, and has the advantages of high yield, high purity, recyclable catalyst, and no need of rectification equipment.

Stereocontrolled Synthesis of Delgocitinib, a JAK Inhibitor for the Treatment of Atopic Dermatitis

Herein is reported the nine-step commercial synthesis of delgocitinib, a Janus kinase inhibitor approved for the treatment of atopic dermatitis in 2020. Its chiral spirodiamine core was selectively constructed by an intramolecular SN2 reaction of the suitably designed γ-lactone substrate and a few subsequent steps including a selective γ-lactone ring-opening reaction with potassium phthalimide, hydrazine-free mild dephthaloylation, and one-pot reduction of β- and γ-lactams. The route affords chemically and stereochemically pure delgocitinib in 39% yield.

Production process of chloropropionyl glutamine

The invention relates to the technical field of chemical engineering, and discloses a production process of chloropropionyl glutamine. The production process comprises following steps: carrying out acylating chlorination reaction: adopting D-2-chloropropionic acid and thionyl chloride as raw materials, adopting DMF (N, N-dimethylformamide) as a catalyst, and carrying out reaction to generate D-2-chloropropionyl chloride, sulfur dioxide and hydrogen chloride. According to the production process of chloropropionyl glutamine, 791kg of thionyl chloride is pressed into a dry and clean 2000 L enamelreaction kettle by using nitrogen, stirring is started, and 0.75kg of N, N-dimethylformamide is slowly dropwise added; then, 600kg of D-2-chloropropionic acid is pressed into a dry and clean 1000L enamel high-level tank by using nitrogen gas, a reaction kettle jacket is subjected to 75 DEG C hot water bath to increase the temperature of the system to 60-65 DEG C, D-2-chloropropionic acid is dropwise added into the reaction kettle for about 4 h at 60 to 65 DEG C, and the gas release amount is controlled by adjusting the dropwise adding speed. T production process is simple in steps, complete in reactant reaction, high in raw material utilization rate and low in preparation cost, troubles of users are avoided, and the production process is convenient for users to use.

Selective PI3Kdelta inhibitor and application thereof

The present application relates to a compound as a selective PI3Kdelta kinase inhibitor comprising a compound of the following formula (I) or a pharmaceutically acceptable salt, solvate, ester, acid,metabolite or prodrug thereof, wherein X, R1, R2, R3, R4, R5 and R6 are as defined in the specification. The present application also relates to methods and uses of using such kinase inhibitor to inhibit PI3Kdelta kinase activity or to treat or prevent diseases or disorders associated with tyrosine kinase activity of PI3Kdelta.

PROCESS FOR PREPARING 7H-PYRROLO[2,3-d]PYRIMIDINE DERIVATIVES AND SYNTHETIC INTERMEDIATES THEREOF

The present invention provides processes for preparing 7H-pyrrolo[2,3-d]pyrimidine derivatives, which are useful as a Janus kinase (JAK) inhibitor, intermediates thereof, and processes for preparing the intermediates. The present invention provides processes for preparing 3-[(3S, 4R)-3-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.4]octan-1-yl]-3-oxopropanenitrile using salts of (3S,4R)-1-benzyl-3-methyl-1,6-diazaspiro[3.4]octane with organic acids.

AN OPTICALLY ACTIVE N- (alpha-MERCAPTOPROPIONY) GLYCINE

An optically active N-(α-mercaptopropionyl)glycine, i.e., R-(-)-N-(α-mercaptopropionyl)glycine or S-(-)-N-(α-mercaptopropionyl)glycine, a preparation method thereof, a pharmaceutical preparation containing the compound or a pharmaceutically acceptable salt or ester thereof, and use of the same in preparation of detoxification medicament for improving metabolism, are provided.

Recovery of ammonia in the dipeptide manufacturing processes

An example of an improvement in recovering ammonia in a dipeptide manufacturing process is described. The synthetic method, which makes use of the ammonolysis reaction, has been studied and found to produce dipeptides of satisfactory quality in high yield on a large scale. However, the treatment of unreacted ammonia in the ammonolysis reaction caused a reduction in the productivity and increased the production cost during actual manufacture. Therefore, a method to recover the unreacted ammonia has been investigated through simulations and trial runs using model solutions. Consequently, the modified process provided an improvement in the productivity and cost savings. In addition, the recovered ammonia could possibly be used for recycling. It was verified in a lab experiment that the reused ammonia did not lower the quality of the dipeptide.

Process research and development of L-alanyl-L-glutamine, a component of parenteral nutrition

A large-scale manufacturing method of L-alanyl-L-glutamine used for a component of parenteral nutrition has been studied. The method consisted of a reaction of D-2-chloro- or D-2-bromopropionic acid with thionyl chloride and Schotten-Baumann reaction with L-glutamine followed by ammonolysis reaction. The intermediate D-2-chloropropionyl-L-glutamine was found to be more stable than its bromo analogue. In the ammonolysis reaction, the former intermediate needed a higher reaction temperature, but the by-products produced had little effect on the quality of the final product. The structures of the by-products were conjectured mainly by mass spectrometry and they were removed by anion resin treatment and recrystallization.

Stereochemical Consequences of Bromine-for-Halogen Substitutions in the Gas Phase

The stereochemistry of translationally excited bromine-for-halogen substitution was studied in gaseous 2(S)- and 2(R)-halopropionyl halides.Net inversion of configuration was observed for 75Br-for-X substitutions with a trend of increasing inversion as the displaced atom was varied in the series, X = F, Cl, Br.A correlation with previous studies on 18F-for-X and 34mCl-for-X substitutions also showed increased inversion with increased mass of the displacing agent.In addition, these recoil atom substitutions showed an apparent independence from the free-energy requirement of reaction.

Stereochemical Consequences of Halogen-for-Halogen Substitutions in the Gas Phase

The stereochemistry of translationally energetic fluorine-for-halogen and chlorine-for-halogen substitution was studied in gaseous 2(S)- and 2(R)-halopropionyl halides.While net inversion of configuration was observed for halogen using 34mCl as the displacing agent, predominant retention of configuration was found when 18F was used as the displacing agent on the chiral centers of the 2-halopropionyl halides.The extent of inversion or retention in these energetic substitution reactions appears to be sensitive to the mass of the incoming atom, to steric hindrance to back-side attack, and to the nature of the halogen leaving group.