7474-05-7

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-2-Chloropropionic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. It serves as a starting material for the preparation of Thiolactic acid, which is crucial for the production of 2(R),5(S)-oxathiolanones by reacting with pivalaldehyde. These oxathiolanones are important in the development of pharmaceutical agents.
Additionally, (R)-(+)-2-Chloropropionic acid is used in the synthesis of (R)-2-chloropropionyl chloride, another key intermediate. (R)-(+)-2-Chloropropionic acid is utilized in the synthesis of (R)-4,5-dihydro-5-methylpyridazin-3(2H)-one derivatives, which possess a pyrazolopyridine ring and act as potential phosphodiesterase inhibitors. Phosphodiesterase inhibitors have therapeutic applications in treating various diseases, including cardiovascular and respiratory disorders.
Used in Biochemical Research:
(R)-(+)-2-Chloropropionic acid is also used in the synthesis of 2-Chloropropionamide derivatives, which function as protein disulfide isomerase (PID) inhibitors. PIDs play a critical role in the regulation of protein folding and redox homeostasis in cells. Inhibition of these enzymes can have potential applications in the study and treatment of various diseases, such as neurodegenerative disorders and cancer, where protein misfolding and oxidative stress are implicated.

InChI:InChI=1/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m1/s1

Upstream product

• 1458-99-7 4-chloropent-2-ene 
• 338-69-2 D-Alanine 
• 42411-39-2 (R)-ethyl 2-chloropropanoate 
• 77287-29-7 methyl (2R)-2-chloropropanoate 
• 129974-79-4 (RS)-1-Pentylpropynyl (D)-2-chloropropanoate 
• 129974-80-7 (RS)-Bicyclo<2.2.1>hept-2-yl (D)-2-chloropropanoate 
• 17639-93-9 2-chloro-propionic acid methyl ester 
• 79-33-4 L-Lactic acid 
• 10026-13-8 phosphorus pentachloride 
• 70836-98-5 (S)-2-(p-toluenesulphonyloxy)propionic acid 
• 67-64-1 acetone 
• 692291-15-9 2-chloropropanal 
• 212568-27-9 (R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester 
• 167937-27-1 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl α-chloropropionate 

Downstream Products

• 77277-24-8 2-((4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-benzyloxycarbonylamino-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 
• 83100-71-4 benzyl 2-acetamido-4-O-<2-acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-3-O-(D-1-carboxyethyl)-2-deoxy-α-D-glucopyranoside 
• 75957-44-7 2-[(4aR,6S,7R,8R,8aS)-7-Acetylamino-6-((2R,3S,4R,5R,6S)-5-acetylamino-4,6-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 
• 75957-44-7 benzyl 2-acetamido-4-O-<2-acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 75957-46-9 2-[(2S,3R,4R,5S,6R)-3-Acetylamino-5-((4aR,6S,7R,8R,8aS)-7-acetylamino-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy]-propionic acid 
• 75957-46-9 benzyl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-6-O-benzyl-3-O-(D-1-carboxyethyl)-α-D-glucopyranoside 
• 81086-80-8 benzyl 2-(N-acetyl-N-methylamino)-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 
• 81086-79-5 benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 
• 85472-20-4 6-(benzyloxycarbonylamino)hexyl 2-acetamido-4,6-O-benzylidene-3-O-(D-1-carboxyethyl)-2-deoxy-β-D-glucopyranoside 
• 197575-01-2 (R)-2-((4aR,6R,7R,8R,8aS)-7-Acetylamino-6-cyclohexyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 
• 197575-02-3 (R)-2-((4aR,6R,7R,8R,8aS)-7-Acetylamino-6-phenethyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 
• 197575-03-4 (R)-2-[(4aR,6R,7R,8R,8aS)-7-Acetylamino-6-(naphthalen-2-ylmethoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 
• 197575-04-5 (R)-2-[(4aR,6R,7R,8R,8aS)-7-Acetylamino-6-(2-naphthalen-1-yl-ethoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid 
• 10326-41-7 D-Lactic acid 

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.

Preparation method of alpha-chloro carboxylic acid

The invention discloses a preparation method of alpha-chloro carboxylic acid. According to the preparation method, amino acids are dissolved into hydrochloric acid to form a homogeneous solution; thenobtained homogeneous solution and a sodium nitrite water solution are simultaneously pumped into a mixing valve through an injection pump A and an injection pump B of a micro-channel reaction apparatus; after the solutions are fully mixed, the mixed solution is pumped into a micro reactor of the micro-channel reaction apparatus to carry out reactions at a constant flowing speed, and the flow-outliquid namely alpha-chloro carboxylic acid is collected. The provided method realizes the continuous production of alpha-chloro carboxylic acid; furthermore, the product quality is good, the operationis simple, the using amount of raw materials is little, the process is safe, the method is green and environmentally friendly, energy is saved, the efficiency is high, and thus the method is suitablefor industrial production.

Method for synthesizing (R)-2-chloropropionic acid by solid acid catalysis and trans-esterification reaction based on UIO-66

The invention provides a method for synthesizing (R)-2-chloropropionic acid by a solid acid catalysis and trans-esterification reaction based on UIO-66. The method comprises the following steps: (1) preparation of a solid acid catalyst SO4/UIO-66; and (2) preparation of (R)-2-chloropropionic acid. According to the method, UIO-66 is adopted as a solid acid catalyst of a substrate, the catalyst has strong acidity, so that the catalyst can effectively catalyze the trans-esterification reaction for synthesizing (R)-2-chloropropionic acid, the transformation rate is higher than 98%, side effects are less, and the catalyst can be used repeatedly, and therefore, the generation of tailings is effectively avoided, the production cost is lowered, and environmental protection is facilitated.

Ester exchange method for preparing high purity R-(+) - 2-chloropropionic acid process of

The invention discloses a process for preparing high-optical-purity R-(+)-2-chloropropionic acid through an ester exchange method. The process comprises the following steps: placing ethyl chloropropionate in a reactor, sequentially adding formic acid with the mass fraction of 94% and strong-acid cation exchange resin under stirring, slowly heating to 54DEG C, extracting ethyl formate, continuously heating, and recovering formic acid; and forming a negative pressure after the recovery of formic acid, and extracting R-(+)-2-chloropropionic acid. The process has the advantages of simple technology, no strong acidic tails, environmental protection and short production period, and the optical purity and the yield of the prepared R-(+)-2-chloropropionic acid are not smaller than 99% and not smaller than 90% respectively.

COMPOUNDS FOR USE IN THE TREATMENT OF INFECTIOUS DISEASES

The present invention relates to compounds of formula (I), wherein R1, R2, R3, R4, R5 and R6 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

Roof shape chiral alcohol: auxiliary for asymmetric synthesis of α-halo acid derivatives

Roof shape chiral enantiopure alcohol, obtained by bio-catalytic separation of isomers, was used as a new auxiliary for asymmetric synthesis of α-halo acid derivatives. Esterification reaction of roof shape chiral enantiopure alcohol and racemic α-halo acids in the presence of DCC, DMAP furnished diastereomers of ester in non-racemic manner. Diastereoselectivity up to 90% was observed, the absolute configuration of newly generated chiral center was established by the single crystal X-ray diffraction analysis.

THIOLACTONE ANTIBIOTICS

This invention provides a compound having the structure (I) wherein R1 is H, (II) or (III), wherein n and q are independently an integer from 0 to 8; A is absent or present and when present is (IV), (V), (VI), (VII), (VIII), or (IX), wherein m is an integer from 0 to 8; R3 is an amino, alkyl, aryl, heteroaryl, diol, piperazine, morpholine, piperidine, triazole, azide or biphenyl, each with or without substitution, branched or unbranched, or (X); and R4 is alkyl, aryl, or heteroaryl, each with or without substitution, branched or unbranched, R2 is H, CH3, or alkyl, aryl, heteroaryl, pyrrole, diazole, or triazole, each with or without substitution, branched or unbranched, or (XI), wherein n and q are independently an integer from 0 to 8; A is absent or present and when present is (IV), (V), (VI), (VII), or (VIII); and R6 is azide, methoxy, trifluoromethyl, biphenyl, substituted phenyl, substituted triazole, or alkyl, aryl or heteroaryl, with or without substitution, branched or unbranched, when R1 is H then R2 is other than H or CH3, and when R2 is H or CH3 then R1 is other than H, or a pharmaceutically acceptable salt thereof.

Direct Organocatalytic Asymmetric α-Chlorination of Aldehydes

The direct organocatalytic enantioselective α-chlorination of aldehydes has been developed. The reaction proceeds for a series of different aldehydes with NCS as the chlorine source using easily available catalysts such as L-proline amide and (2R,5R)-diphenylpyrrolidine. The α-chloro aldehydes are obtained in up to 99% yield and up to 95% ee. The synthetic utility of the enantioselective α-chlorination of aldehydes is demonstrated by transformation of the α-chloro aldehydes to the corresponding α-chloro alcohols (>90% yield) by standard reduction and further transformation to both a terminal epoxide and amino alcohol, both obtained without loss of optical purity. Oxidation of the α-chloro aldehydes followed by esterification gave optically active α-chloro esters without loss of optical purity. It is demonstrated that these optically active α-chloro esters can be converted into nonproteinogenic amino acids in overall high yields, maintaining the enantiomeric excess obtained in the catalytic enantioselective α-chlorination step. Copyright

Design and synthesis of chromogenic thiopeptolide substrates as MetAPs active site probes

Twenty one chromogenic thiopeptolide substrates were designed and synthesized as the active site probes and analyzed with each S1 site of mutant residues and enzymes of wild-type MetAP1s. The preliminary enzymatic experiments indicate that cysteine 70 or 202, at either Escherichia coli or human MetAP1, played a crucial role in the methionine hydrolysis.

A flexible route to (5R)-thiolactomycin, a naturally occurring inhibitor of fatty acid synthesis.

[formula: see text] A new and efficient asymmetric synthesis of naturally occurring (5R)-thiolactomycin (1) using D-alanine as the source of chirality is described.