627-03-2

Basic information

• Product Name: Ethoxyacetic acid
• Synonyms: 2-Ethoxyacetic acid;2-ethoxyaceticacid;Aceticacid,ethoxy-;ethoxy-aceticaci;Ethoxyethanoicacid;Glycolic ethyl ether;Ethoxyacetic acid,98%;Ethoxyacetic acid,O-Ethylglycolic acid
• CAS NO: 627-03-2
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.1
• EINECS: 210-978-2
• Product Categories: Building Blocks;C1 to C5;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Acetics acid and esters;Organic acids
• Mol File: 627-03-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 97-100 °C11 mm Hg(lit.)
• Flash Point: 208 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.102 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0958mmHg at 25°C
• Refractive Index: n20/D 1.419(lit.)
• Storage Temp.: 2-8°C
• PKA: 3.65(at 18℃)
• Water Solubility: soluble
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1743037
• CAS DataBase Reference: Ethoxyacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Ethoxyacetic acid(627-03-2)
• EPA Substance Registry System: Ethoxyacetic acid(627-03-2)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• RTECS: AH3600000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 627-03-2(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

Ethoxyacetic acid is used to evaluate toxicity in embryonic stem cell test in mice. It finds application as a biomarker of exposure to alkyl-substituted ethylene glycols and other aliphatic ethers. It is used as a precursor to prepare ethoxy-acetic acid ethoxymethyl ester.

General Description

Liquid.

Air & Water Reactions

Water soluble.

Reactivity Profile

An ether and organic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat.

Health Hazard

ACUTE/CHRONIC HAZARDS: Ethoxyacetic acid is corrosive.

Fire Hazard

Ethoxyacetic acid is combustible.

Biochem/physiol Actions

Ethoxyacetic acid induces testicular toxicity in rats in vivo .

InChI:InChI=1/C4H8O3/c1-2-7-3-4(5)6/h2-3H2,1H3,(H,5,6)/p-1

Synthetic route

2-ethoxy-ethanol (110-80-5) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With sodium persulfate; sodium bis(1,2-dicarbollyl)cobaltate(III); potassium carbonate In water for 8h; pH=7; Irradiation;	97%
With sodium hydroxide; potassium hexacyanoferrate(III) at 30℃; Kinetics; Further Variations:; substrate and reagents concentration dependence; Oxidation;
With Jones reagent In acetone at 20℃;
With sodium hydroxide; cadmium(II) oxide at 225 - 250℃; im Kupferautoklaven;
With sodium persulfate; C25H21N5ORu(2+)*2C4H22B18Co(1-); potassium carbonate In water at 20℃; for 8h; Catalytic behavior; Inert atmosphere; UV-irradiation;

ethanol (64-17-5) + sodium monochloroacetic acid (3926-62-3) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
Stage #1: ethanol With sodium at 60℃; Stage #2: sodium monochloroacetic acid With N-benzyl-N,N,N-triethylammonium chloride for 8h; Reflux;	76%
With sodium hydride

sodium ethanolate (141-52-6) + chloroacetic acid (79-11-8) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
In ethanol	70%

ethanol (64-17-5) + chloroacetic acid (79-11-8) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With sodium ethanolate at 80℃; for 0.166667h;	61%
With sodium hydride 1.) 1 h, 2.) reflux, 1 h; Yield given. Multistep reaction;
With sodium ethanolate Reflux;

ethyl 2-ethoxyethanoate (817-95-8) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; for 12h;	5%

2-ethoxyacetonitrile (62957-60-2) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With hydrogenchloride

ethoxyacetaldehyde (22056-82-2) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With barium dihydroxide; silver nitrate

ethoxyethylamide (51770-98-0) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With nitrogen oxides at 90℃;

1,6-diethoxy-hexa-2t,4t-diene → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With chloroform; ozone und Zersetzung des Ozonidgemisches mit warmem Wasser;

1-ethoxy-2,4-pentanedione (20754-01-2) → ethoxy-2-propanone (14869-34-2) + 3-oxapentanoic acid (627-03-2) + acetic acid (64-19-7) + acetone (67-64-1)

Conditions	Yield
Hydrolysis;

ethanol (64-17-5) + sodium ethanolate (141-52-6) + chloroacetic acid (79-11-8) → 3-oxapentanoic acid (627-03-2)

carbon dioxide (124-38-9) + ethoxymethylmagnesium chloride (4279-03-2) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
In tetrahydrofuran at -60℃;

carbon monoxide (201230-82-2) + orthoformic acid triethyl ester (122-51-0) → diethyl ether (60-29-7) + formaldehyde diethyl acetal (462-95-3) + 3-oxapentanoic acid (627-03-2) + ethyl 2-ethoxyethanoate (817-95-8) + Ethyl propionate (105-37-3) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With rhodium(III) chloride; hydrogen; methyl iodide; dicarbonyldiiodorhodate(I) anion at 170℃; under 60004.8 Torr; Product distribution; Mechanism; var. temp.; H2/CO ratio and catalysts (chlorocarbonylrhodium; carbonylrhodium);	A 29.3 mmol B 135.2 mmol C 3.3 mmol D 4.5 mmol E 22.1 mmol F 55.0 mmol

Ethoxy-(2-ethoxy-acetoxy)-acetic acid ethyl ester → ethyl 2-ethoxyglycolate (49653-17-0) + 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With pancrease lipase In hexane; water at 30℃; for 2h;

diethyl ether (60-29-7) → ethoxyacetaldehyde (22056-82-2) + 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With tert.-butylhydroperoxide; triphenylbismuthane at 10 - 15℃; for 20h; Product distribution; various reaction times;

carbon dioxide (124-38-9) + ethyl chloromethyl ether (3188-13-4) → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; lithium 1.) THF, -90 deg C, 2.) THF, from -90 deg C to -60 deg C, 4 h; Yield given. Multistep reaction;

1,4-diethoxy-2-butene (71972-32-2) + alkaline KMnO4 → 3-oxapentanoic acid (627-03-2)

1,4-diethoxy-2-chloro-but-2-ene (157198-16-8) + alkaline KMnO4 → 3-oxapentanoic acid (627-03-2)

ethyl 2-ethoxyethanoate (817-95-8) + calcium hydroxide → 3-oxapentanoic acid (627-03-2)

1,1,1,2-tetrachoroethane (630-20-6) + NaOC2H5 → 3-oxapentanoic acid (627-03-2)

(E)-1,2-dichloro-1-ethoxy-ethene (42345-82-4) + NaOC2H5 → 3-oxapentanoic acid (627-03-2)

chloroacetic acid (79-11-8) + NaOC2H5 → 3-oxapentanoic acid (627-03-2)

Conditions	Yield
With ethanol

ethyl 2-ethoxyethanoate (817-95-8) + hydrogen bromide (10035-10-6, 12258-64-9) → glycolic Acid (79-14-1) + 3-oxapentanoic acid (627-03-2)

Conditions	Yield
at 100℃;

chloroform (67-66-3) + 1,6-diethoxy-hexa-2t,4t-diene + ozone (10028-15-6) → ethoxyacetaldehyde (22056-82-2) + 3-oxapentanoic acid (627-03-2) + 4-ethoxy-crotonaldehyde + γ-ethoxy-crotonic acid

Conditions	Yield
und nachfolgendes Zersetzung des Reaktionsprodukts mit warmem Wasser;

hydrogenchloride (7647-01-0) + ethoxyethylamide (51770-98-0) → 3-oxapentanoic acid (627-03-2) + ammonium chloride

N-ethoxyacetyl-N'-ethoxymethyl-urea (861616-31-1) + acid → formaldehyd (50-00-0) + ethanol (64-17-5) + 3-oxapentanoic acid (627-03-2) + ammonia (7664-41-7)

Conditions	Yield
Produkt 5:Kohlensaeure;

N-ethoxyacetyl-N'-ethoxymethyl-urea (861616-31-1) + alkali → formaldehyd (50-00-0) + ethanol (64-17-5) + 3-oxapentanoic acid (627-03-2) + ammonia (7664-41-7)

Conditions	Yield
Produkt 5:Kohlensaeure;

4-ethoxy-3-hydroxy-butyraldehyde + KMnO4 + alkali → 3-oxapentanoic acid (627-03-2) + oxalic acid (144-62-7)

ethyl-hexa-2,3,4-trienyl ether (412344-87-7) + ozone (10028-15-6) → formic acid (64-18-6) + 3-oxapentanoic acid (627-03-2) + acetic acid (64-19-7)

3-oxapentanoic acid (627-03-2) + phenylmethanethiol (100-53-8) → benzyl ethoxyethanothioate (32363-07-8)

Conditions	Yield
With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature;	100%

7-methyl-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnoline-5-ol (708984-65-0) + 3-oxapentanoic acid (627-03-2) → 5-ethoxyacetyloxy-7-methyl-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnoline

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1-methyl-pyrrolidin-2-one; DMF (N,N-dimethyl-formamide) at 20℃;	98.8%

phenylthiomethyl chloride (7205-91-6) + 3-oxapentanoic acid (627-03-2) → (phenylthio)methyl 2-ethoxyacetate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 90℃; for 1.5h;	97%

3-oxapentanoic acid (627-03-2) + dehydroepiandrosterone (53-43-0) → 3β-(3'-oxapentanoyloxy)-androst-5-en-17-one (1339841-70-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 2h;	96.1%

3-oxapentanoic acid (627-03-2) + 23,24-dihydrocucurbitacin F 25-O-acetate → 2,3,16-tri-O-2'-ethoxyacetyl-hemslecin A (1424038-80-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	93%

3-oxapentanoic acid (627-03-2) + 5β,6β-epoxy-hemslecin A (1424038-86-7) → 2,3,16-tri-O-2'-ethoxyacetyl-5β,6β-epoxy-hemslecin A (1424038-99-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	93%

3-oxapentanoic acid (627-03-2) → ethoxyacetyl chloride (14077-58-8)

Conditions	Yield
With thionyl chloride In dichloromethane at 4 - 20℃; for 2h;	92%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 25℃; for 2h;	76.42%
With thionyl chloride In dichloromethane at 0 - 20℃; for 2h;	75%

methanol (67-56-1) + 3-oxapentanoic acid (627-03-2) → Ethoxyessigsaeure-methylester (17640-26-5)

Conditions	Yield
With thionyl chloride at 0℃;	91%
With sulfuric acid

(8E,12E,14E)-7-acetoxy-6,21-bis(1-ethoxyethoxy)-3-hydroxy6,20,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide + 3-oxapentanoic acid (627-03-2) → (8E,12E,14E)-7-acetoxy-3-ethoxyacetoxy-6,21-bis(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	91%

3-oxapentanoic acid (627-03-2) + 2-hydroxy-5-chloro-aniline (95-85-2) → C10H12ClNO3

Conditions	Yield
With boric acid In toluene for 4h; Dean-Stark; Reflux; Green chemistry; chemoselective reaction;	90%

3-oxapentanoic acid (627-03-2) + 2-<5-amino-2-(trifluoromethyl)phenyl>-5-n-butyl-4-<<2'-(N-tert-butylsulfamoyl)-3-fluorobiphenyl-4-yl>methyl>-2,4-dihydro-3H-1,2,4-triazol-3-one (170647-84-4) → 5-n-butyl-4-<<2'-(N-tert-butylsulfamoyl)-3-fluorobiphenyl-4-yl>methyl>-2,4-dihydro-2-<5-<(ethoxyacetyl)amino>-2-(trifluoromethyl)phenyl>-3H-1,2,4-triazol-3-one (170647-85-5)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane Ambient temperature;	88%

oxalyl dichloride (79-37-8) + 3-oxapentanoic acid (627-03-2) + pomalidomide (19171-19-8) → N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-2-ethoxy-acetamide (444288-18-0)

Conditions	Yield
In tetrahydrofuran; methanol; N,N-dimethyl-formamide	87%
In tetrahydrofuran; methanol; N,N-dimethyl-formamide	87%

3-oxapentanoic acid (627-03-2) + 11,23,24-tri-O-acetyl-alisol A (19885-11-1) → 11,23,24-tri-O-acetyl-25-ethoxyacetyl-alisol A (1202531-42-7)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	87%

4-amino-5-chloro-2,1,3-benzothiadiazole (30536-19-7) + 3-oxapentanoic acid (627-03-2) + N-acetyl-2-ethylthio-2-imidazoline (61076-80-0) → tizanidine ethoxyacetate

Conditions	Yield
In methanol; N,N-dimethyl-formamide at -5 - 70℃; for 24h;	86.5%

(8E,12E,14E)-7-acetoxy-3-t-butyldimethylsiloxy-6,21-dihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (445488-04-0) + 3-oxapentanoic acid (627-03-2) → (8E,12E,14E)-7-acetoxy-3-t-butyldimethylsiloxy-21-ethoxyacetoxy-6-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;	85%

3-oxapentanoic acid (627-03-2) + camptothecin (7689-03-4) → camptothecin-20-O-ethyloxyacetate (401478-58-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h;	84.7%

1,1-Diphenylmethanol (91-01-0) + 3-oxapentanoic acid (627-03-2) → benzhydryl 2-ethoxyacetate (1427701-68-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	83%

3-oxapentanoic acid (627-03-2) + caudatin → 3-O-(ethoxyacetyl)caudatin (1377496-26-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	81.7%

chlorotetra-acetatodiruthenium + 3-oxapentanoic acid (627-03-2) → Ru2Cl(μ-2-ethoxyacetate)4 * H2O

Conditions	Yield
In methanol; water inert atmosphere; in 50% MeOH, excess carboxylic acid, refluxing for 4 h, evapn. (vac.), washing (petroleum ether), refluxing with fresh ligand in 50% MeOH for 4 h; evapn., recrystn. (CH2Cl2/petroleum ether, then aq. MeOH); elem. anal.;	81%

3-oxapentanoic acid (627-03-2) + 11,23,24-tri-O-2'-ethoxyacetyl-alisol A (1159410-32-8) → 11,23,24,25-tetra-O-2'-ethoxyacetyl-alisol A (1159410-33-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	81%

3-oxapentanoic acid (627-03-2) + 22,23-dihydrocucurbitacin F (50298-90-3) → C42H66O13 (1424039-14-4) + C46H72O15 (1424039-17-7)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	A 80% B 24%

3-oxapentanoic acid (627-03-2) + C21H22N4O2S → 2-((4,6-Dimethylpyrimidine-2-yl)thio)-N-(3-((4-(2-ethoxyacetamido)phenoxy)methyl) phenyl)acetamide

Conditions	Yield
With benzotriazol-1-ol; bromoacetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;	80%

3-oxapentanoic acid (627-03-2) + 13β,17β-epoxy-alisol A (142808-08-0) → 11,23,24,25-tetra-O-2'-ethoxyacetyl-13β,17β-epoxy-alisol A (1159410-47-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	79%

ethanol (64-17-5) + 3-oxapentanoic acid (627-03-2) → ethyl 2-ethoxyethanoate (817-95-8)

Conditions	Yield
With sulfuric acid at 100℃; for 2h; Inert atmosphere;	78%
With toluene-4-sulfonic acid for 12h; Reflux;	73%
With hydrogenchloride
With sulfuric acid; benzene

3-oxapentanoic acid (627-03-2) + ethyl 2-bromo-2-ethoxy-acetate (57941-45-4) → Ethoxy-(2-ethoxy-acetoxy)-acetic acid ethyl ester

Conditions	Yield
With triethylamine In dichloromethane for 4h; Heating;	78%

C6H4NCH2CHCCH2 (491-35-0) + 3-oxapentanoic acid (627-03-2) → 2-(ethoxymethyl)-4-methylquinoline

Conditions	Yield
With cerium(III) chloride heptahydrate; tetrabutyl-ammonium chloride In 2,2,2-trifluoroethanol for 17h; Schlenk technique; Inert atmosphere; Electrochemical reaction; Irradiation;	78%

3-oxapentanoic acid (627-03-2) + 7-deacetyl forskolin (64657-20-1) → 8,13-epoxy-7β-ethoxyacetoxy-1α,6β,9α-trihydroxylabd-14-en-11-one + 1α,7β-bis-ethoxyacetoxy-6β,9α-dihydroxy-8,13-epoxylabd-14-en-11-one

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate for 3h; Ambient temperature;	A 76.23% B 11%

3-oxapentanoic acid (627-03-2) + isopropyl alcohol (67-63-0) → isopropyl 2-ethoxyacetate (54063-13-7)

Conditions	Yield
for 12h; Reflux;	76%
With hydrogenchloride

Upstream product

• 62957-60-2 2-ethoxyacetonitrile 
• 22056-82-2 ethoxyacetaldehyde 
• 51770-98-0 ethoxyethylamide 
• 124-38-9 carbon dioxide 
• 4279-03-2 ethoxymethylmagnesium chloride 
• 60-29-7 diethyl ether 
• 3188-13-4 ethyl chloromethyl ether 
• 67-66-3 chloroform 
• 10028-15-6 ozone 
• 412344-87-7 ethyl-hexa-2,3,4-trienyl ether 
• 64-17-5 ethanol 
• 79-08-3 bromoacetic acid 
• 817-95-8 ethyl 2-ethoxyethanoate 
• 861616-31-1 N-ethoxyacetyl-N'-ethoxymethyl-urea 

Downstream Products

• 817-95-8 ethyl 2-ethoxyethanoate 
• 50-00-0 formaldehyd 
• 462-95-3 formaldehyde diethyl acetal 
• 64-17-5 ethanol 
• 14077-58-8 ethoxyacetyl chloride 
• 100950-30-9 ethoxy-acetic acid-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamide) 
• 14521-87-0 ethoxyacetic anhydride 
• 86321-58-6 2-ethoxymethyl-1,3-benzothiazole 
• 57941-81-8 ethoxy-acetic acid phenyl ester 
• 17640-26-5 Ethoxyessigsaeure-methylester 
• 32152-61-7 N-[4-(3-cyclohexyl-2-imino-imidazolidine-1-sulfonyl)-phenethyl]-2-ethoxy-acetamide 
• 201230-82-2 carbon monoxide 
• 79-14-1 glycolic Acid 
• 75-03-6 ethyl iodide 

Relevant articles and documents

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The invention is directed to substituted bridged cycloalkane derivatives. Specifically, the invention is directed to compounds according to Formula (I) wherein X, a, b, C, D, L2,L3, Y1, Y2, R2, R4, R5, R6, z2, z4, z5, and z6 are as defined herein, and salts thereof. The invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to compounds for use in methods of inhibiting the ATF4 (activating transcription factor 4) pathway and treatment of disorders associated therewith, such as e.g. cancer, neurodegenerative diseases and many other diseases, using a compound of the invention or a pharmaceutical composition comprising a compound of the invention. Preferred compounds of the invention are N-(3-(2-(4-chlorophenoxy) acetamido)bicyclo[1.1.1]pentan-l-yl)-2-cyclobutane-l-carboxamide derivatives and related compounds.

Isopropyl 2-ethoxyacetate—an efficient acylating agent for lipase-catalyzed kinetic resolution of amines in batch and continuous-flow modes

Productivity [conversion (c) and specific reaction rate (rbatchor rflow)] and enantiomer selectivity [enantiomeric ratio (E) and enantiomeric excess (ee) of the products] of ethyl and isopropyl esters of acetic, 2-methoxyacetic and 2-ethoxyacetic acids as acylating agents were compared in the N-acylation of (±)-1-phenylethanamine rac-1 catalyzed by variously immobilized forms of Candida antarctica lipase B (CaLB) using shake flasks and continuous-flow reactors. The effect of the temperature in the 0–80 °C range on productivity and enantiomer selectivity in KRs of rac-1 was investigated with the isopropyl esters in continuous-flow mode using CaLB-filled minireactors. Isopropyl 2-ethoxyacetate surpassed the performance of ethyl 2-methoxyacetate in terms of both productivity (1.9–2.9 times higher rate in batch mode) and enantiomeric selectivity (ee(R)-amide>99.9% compared to 99.8%) providing at 40 °C high volumetric productivity (2.22 kg L?1h?1), specific reaction rate and enantiomeric excess (rflow=783 μmol min?1g?1, ee(R)-2c>99.9%).