6938-26-7

Usage

Uses

Used in Pharmaceutical Industry:
DL-ALPHA-HYDROXYVALERIC ACID ETHYL ESTER is used as an intermediate for the synthesis of 6-(2,4-diaminopyrimidinyl)-1,4-benzoxazin-3-ones, which are small molecule renin inhibitors. These renin inhibitors play a crucial role in the treatment of hypertension and other cardiovascular diseases by blocking the renin-angiotensin system, thus reducing blood pressure and the risk of heart attacks and strokes.

InChI:InChI=1/C18H13NO3/c1-12-10-16(8-9-17(12)20)19-22-18(21)15-7-6-13-4-2-3-5-14(13)11-15/h2-11H,1H3

Upstream product

• 64-17-5 ethanol 
• 617-31-2 2-hydroxyvaleric acid 
• 74-90-8 hydrogen cyanide 
• 123-72-8 butyraldehyde 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 50461-74-0 ethyl 2-oxovalerate 
• 75-03-6 ethyl iodide 
• 924-44-7 glyoxylic acid ethyl ester 
• 17745-45-8 propylboronic acid 
• 2450-71-7 Propargylamine 
• 615-83-8 2-bromo-pentanoic acid ethyl ester 
• 584-93-0 2-Bromovaleric acid 
• 5699-72-9 1-Cyanobutanol 

Downstream Products

• 1003855-66-0 2-hydroxy-valeric acid anilide 
• 29117-54-2 (S)-(-)-1,2-pentanediol 
• 54639-21-3 3-phenyl-5-propyl-oxazolidine-2,4-dione 
• 6302-57-4 5-propyl-oxazolidine-2,4-dione 
• 1208982-46-0 ethyl (R)-2-(diphenylacetyloxy)pentanoate 
• 1208982-47-1 ethyl (S)-2-(diphenylacetyloxy)pentanoate 
• 115626-59-0 ethyl (2S)-2-hydroxypentanoate 
• 88945-70-4 (S)-ethyl 2-hydroxypentanoate 
• 97915-40-7 (5E,7Z,13E)-5,7,13-Pentadecatriene-9,11-diyn-4-ol 
• 5343-92-0 1,2-pentanediol 
• 1578-56-9 2-fluoropentanoic acid 
• 816-26-2 ethyl 2-fluoropentanoate 
• 1448338-50-8 di(1-naphthyl)methyl (S)-2-[(1,1'-biphenyl)-2-yloxy]pentanoate 
• 1448338-52-0 (R)-2-[(1,1'-biphenyl)-2-yloxy]pentanoic acid 

Relevant academic research and scientific papers

Asymmetric Synthesis of N-Substituted α-Amino Esters from α-Ketoesters via Imine Reductase-Catalyzed Reductive Amination

N-Substituted α-amino esters are widely used as chiral intermediates in a range of pharmaceuticals. Here we report the enantioselective biocatalyic synthesis of N-substituted α-amino esters through the direct reductive coupling of α-ketoesters and amines employing sequence diverse metagenomic imine reductases (IREDs). Both enantiomers of N-substituted α-amino esters were obtained with high conversion and excellent enantioselectivity under mild reaction conditions. In addition >20 different preparative scale transformations were performed highlighting the scalability of this system.

SARTAN ANALOGUE

The invention concerns a sartan analogue on basis of a sartan which sartan comprises an alkyl group or an alkoxy group, wherein the sartan analogue only differs from the sartan by a replacement of the alkyl group or the alkoxy group or replacement of a methyl residue or a hydrogen residue of the alkyl group or of the alkoxy group by a fluorine atom.

A method for synthesis of 1, 2 - pentanediol (by machine translation)

The invention relates to the field of organic synthetic technology, in particular to a 1, 2 - pentanediol synthetic method, comprises the following steps: (1) heating the raw material-butyraldehyde, adjusting the pH after adding the hydrocyanic acid, obtained by the reaction of 2 - hydroxy pentanonitrile; (2) taking step (1) in 2 - hydroxy pentanonitrile, adding an alcohol as a solvent to stir and mix, add water to stir and mix, hydrogen chloride gas, in 5 °C the following reaction under the condition for a period of time, to continue the reaction temperature, after the reaction product after the neutralization reaction, centrifugal separation, obtained after the distillation is 2 - hydroxy valeric acid ester compound; (3) heating the step (2) in 2 - hydroxy valeric acid ester compound, under the effects of catalyst after hydrogenation reaction to obtain the 1, 2 - pentanediol. Using the synthesis method of the invention, the 1, 2 - pentanediol yield, and reduces the production cost. (by machine translation)

Enantioselective catalytic synthesis of ethyl mandelate derivatives using Rh(I)-NHC catalysts and organoboron reagents

Herein we describe for the first time the enantioselective catalytic arylation of ethyl glyoxalate using phenylboron reagents and chiral rhodium(I)-NHC catalysts. KOtBu was the base of choice, along with tert-amyl alcohol as the solvent. A novel chiral bis-imidazolium salt was synthesized and evaluated for the first time in this catalytic transformation. Although moderate enantioselectivities (up to 34% ee) were obtained for the phenylation reaction, despite the excellent yields, very low enantioselectivities were obtained using other arylboronic acids with a variety of chiral rhodium(I)-NHC catalysts.

Expeditious and novel synthesis of α-hydroxyesters via rhodium-NHC catalyzed arylation of ethyl glyoxalate

The rhodium-NHC catalyzed arylation reaction of ethyl glyoxalate with aryl and alkyl boronic acids provides an efficient method for the synthesis of α-hydroxyesters. A wide range of α-hydroxyesters (up to 12) were prepared in good to excellent yields. KOtBu was the base of choice, along with tert-amyl alcohol as the solvent. As far as we are aware, this is the first report of this catalytic arylation, using rhodium-NHC catalysts with this specific substrate type.

Stereoselective reduction of carbonyl compounds with actinomycete: Purification and characterization of three α-keto ester reductases from Streptomyces avermitilis

We achieved the purification of three α-keto ester reductases (Streptomyces avermitilis keto ester reductase, SAKERs-I, -II, and -III) from Streptomyces avermitilis NBRC14893 whole cells. The molecular masses of the native SAKERs-I, -II, and -III were estimated to be 72, 38, and 36 kDa, respectively, by gel filtration chromatography. The subunit molecular masses of SAKERs-I, -II, and -III were also estimated to be 32, 32, and 34 kDa, respectively, by SDS-polyacrylamide gel electrophoresis. The purified SAKERs-II and -III showed a reducing activity for α-keto esters (in particular, for ethyl pyruvate). SAKER-I showed a high reducing activity not only toward the α- and β-keto esters, but also toward α-keto acid. The N-terminal region amino acid sequences of SAKERs-I, -II, and -III were identical to that of a putative oxidoreductase, SAV2750, a putative oxidoreductase, SAV1849, and a putative oxidoreductase, SAV4117, respectively, hypothetical proteins coded on the S. avermitilis genome.

PROCESS FOR PRODUCTION OF 2-HYDROXY ESTERS

The invention provides an easy and simple process for the production of 2-hydroxy esters from cyanohydrins, specifically, a process for the production of 2-hydroxy esters represented by the general formula (1) (exclusive of ethyl 2-hydroxy-4-phenylbutyrate), characterized by introducing an acid into a mixture comprising a cyanohydrin represented by the general formula (2), an alcohol, an organic solvent and water: [Chemical formula 1] R1 -CH(OH)-COOR2 (1) R1 -CH(OH)(CN) (2) wherein R1 is hydrogen, a substituted or unsubstituted aliphatic hydrocarbon group which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, a substituted or unsubstituted alicyclic hydrocarbon group which has 3 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, or a substituted or unsubstituted aryl or aralkyl group which has 3 to 14 carbon atoms and may contain oxygen, sulfur, or nitrogen; and R2 is alkyl which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen.

The bakers' yeast reductions of α- and β-keto ester derivatives in the presence of a sulfur compound

Improvement of the enantioselectivity and enhancement of the reactivity were achieved in the bakers' yeast reduction of the α- and β-keto ester derivatives by the addition of a sulfur compound. High enantioselectivity in the bakers' yeast reduction of keto esters was accomplished by using combination of an addition of a sulfur compound with an appropriate selection of the alcohol part of the ester.