← Back to patent-cliff list
CAS 95-92-1
Oxalic acid diethyl diesterdiethyl oxalateEthyl 2-ethoxy-2-oxoacetate
Codes: Enalapril-025, GRAZ-002, Cilastatin Sodium-014, LPHE-002
Application context (from source-drug indications)
Cardiac and vascular disordersAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHypertensionAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHyperlipidaemiaAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHeart diseaseAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHepatitis CGrazoprevir HydrateHIV infectionGrazoprevir HydrateChronic hepatitis CGrazoprevir HydrateRenal impairmentGrazoprevir HydrateEssential hypertensionEnalapril Maleate/Folic AcidHeart failureEnalapril MaleateHypertensionEnalapril MaleateMyocardial infarctionEnalapril MaleateAngina pectorisEnalapril MaleateLeft ventricular dysfunctionEnalapril MaleateSolid tumourEnalapril MaleateInfectious diseaseCilastatin Sodium晕动病L-Phencynonate HydrochlorideCerebral infarctionL-Phencynonate HydrochlorideVertigoL-Phencynonate Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Atorvastatin/Hydrochlorothiazide/Aspirin/Enalapril | Tier C — Watch / trade | - |
| Grazoprevir Hydrate | Tier C — Watch / trade | - |
| Enalapril Maleate/Folic Acid | Tier C — Watch / trade | - |
| Enalapril Maleate | Tier C — Watch / trade | - |
| Cilastatin Sodium | Tier C — Watch / trade | - |
| L-Phencynonate Hydrochloride | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
Atorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilOptimised routesteps: 6total yield: 174mg(Enalapril-033)
(2-Bromoethyl)benzene→Bromido(2-phenylethyl)magnesium→Oxalic acid diethyl diester→2-Oxo-4-phenylbutyric acid ethyl ester→4,5-Ditritium-L-proline→L-Alanine→N-(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanine→N-Hydroxysuccinimide→Ethyl 2-([(2S)-1-[(2,5-dioxopyrrolidin-1-yl)oxy]-1-oxopropan-2-yl]amino)-4-phenylbutanoate→N-(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl-4,5-ditritium-L-proline→(2Z)-But-2-enedioic acid N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-4,5-ditritium-L-proline
4-methoxybenzene-1,2-diamine dihydrochloride→diethyl oxalate→6-methoxyquinoxaline-2,3-diol→3-chloro-7-methoxyquinoxalin-2-ol→(2S,4S)-1-tert-butyl 2-methyl 4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate→1-(tert-butyl) 2-methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate→methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-2-carboxylate hydrochloride→(R)-3,3-dimethyl-2-((((1R,2R)-2-(pent-4-en-1-yl)cyclopropoxy)carbonyl)amino)butanoic acid→methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-1-((S)-3,3-dimethyl-2-((((1R,2R)-2-(pent-4-en-1-yl)cyclopropoxy)carbonyl)amino)butanoyl)pyrrolidine-2-carboxylate→potassium trifluoro(vinyl)borate→methyl (2S,4R)-1-((S)-3,3-dimethyl-2-((((1R,2R)-2-(pent-4-en-1-yl)cyclopropoxy)carbonyl)amino)butanoyl)-4-((7-methoxy-3-vinylquinoxalin-2-yl)oxy)pyrrolidine-2-carboxylate→GRAZ-012→methyl (33R,35S,91R,92R,5S,E)-5-(tert-butyl)-17-methoxy-4,7-dioxo-2,8-dioxa-6-aza-1(2,3)-quinoxalina-3(3,1)-pyrrolidina-9(1,2)-cyclopropanacyclotetradecaphan-13-ene-35-carboxylate→methyl (33R,35S,91R,92R,5S)-5-(tert-butyl)-17-methoxy-4,7-dioxo-2,8-dioxa-6-aza-1(2,3)-quinoxalina-3(3,1)-pyrrolidina-9(1,2)-cyclopropanacyclotetradecaphane-35-carboxylate→(33R,35S,91R,92R,5S)-5-(tert-butyl)-17-methoxy-4,7-dioxo-2,8-dioxa-6-aza-1(2,3)-quinoxalina-3(3,1)-pyrrolidina-9(1,2)-cyclopropanacyclotetradecaphane-35-carboxylic acid→(1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride→(33R,35S,91R,92R,5S)-5-(tert-butyl)-N-((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-17-methoxy-4,7-dioxo-2,8-dioxa-6-aza-1(2,3)-quinoxalina-3(3,1)-pyrrolidina-9(1,2)-cyclopropanacyclotetradecaphane-35-carboxamide→but-3-en-1-ylmagnesium bromide→acrylaldehyde→(E)-(hepta-1,6-dien-1-yloxy)trimethylsilane→trimethyl(2-(pent-4-en-1-yl)cyclopropoxy)silane→2-(pent-4-en-1-yl)cyclopropan-1-ol→(1R,2R)-2-(pent-4-en-1-yl)cyclopropyl acetate→(1R,2R)-2-(pent-4-en-1-yl)cyclopropan-1-ol→methyl (S)-2-isocyanato-3,3-dimethylbutanoate→methyl (S)-3,3-dimethyl-2-((((1R,2R)-2-(pent-4-en-1-yl)cyclopropoxy)carbonyl)amino)butanoate
diethyl oxalate→methyl (33R,35S,91R,92R,5S,E)-5-(tert-butyl)-17-methoxy-4,7-dioxo-2,8-dioxa-6-aza-1(2,3)-quinoxalina-3(3,1)-pyrrolidina-9(1,2)-cyclopropanacyclotetradecaphan-13-ene-35-carboxylate→methyl (33R,35S,91R,92R,5S)-5-(tert-butyl)-17-methoxy-4,7-dioxo-2,8-dioxa-6-aza-1(2,3)-quinoxalina-3(3,1)-pyrrolidina-9(1,2)-cyclopropanacyclotetradecaphane-35-carboxylate→but-3-en-1-ylmagnesium bromide→(1R,2R)-2-(pent-2-yn-1-yl)cyclopropan-1-ol→(R)-3,3-dimethyl-2-((((1R,2R)-2-(pent-2-yn-1-yl)cyclopropoxy)carbonyl)amino)butanoic acid→ethyl 2-oxohex-5-enoate→4-methoxybenzene-1,2-diamine→3-(but-3-en-1-yl)-7-methoxyquinoxalin-2-ol→2-(but-3-en-1-yl)-3-chloro-6-methoxyquinoxaline→1-(tert-butyl) 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate→1-(tert-butyl) 2-methyl (2S,4R)-4-((3-(but-3-en-1-yl)-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate→methyl (2S,4R)-4-((3-(but-3-en-1-yl)-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-2-carboxylate→(S)-3,3-dimethyl-2-((((1R,2R)-2-((Z)-pent-2-en-1-yl)cyclopropoxy)carbonyl)amino)butanoic acid→methyl (2S,4R)-4-((3-(but-3-en-1-yl)-7-methoxyquinoxalin-2-yl)oxy)-1-((S)-3,3-dimethyl-2-((((1R,2R)-2-((Z)-pent-2-en-1-yl)cyclopropoxy)carbonyl)amino)butanoyl)pyrrolidine-2-carboxylate→GRAZ-042
(2-Bromoethyl)benzene→Bromido(2-phenylethyl)magnesium→Oxalic acid diethyl diester→2-Oxo-4-phenylbutyric acid ethyl ester→4,5-Ditritium-L-proline→L-Alanine→N-(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanine→N-Hydroxysuccinimide→Ethyl 2-([(2S)-1-[(2,5-dioxopyrrolidin-1-yl)oxy]-1-oxopropan-2-yl]amino)-4-phenylbutanoate→N-(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl-4,5-ditritium-L-proline→(2Z)-But-2-enedioic acid N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-4,5-ditritium-L-proline
(2-Bromoethyl)benzene→Bromido(2-phenylethyl)magnesium→Oxalic acid diethyl diester→2-Oxo-4-phenylbutyric acid ethyl ester→4,5-Ditritium-L-proline→L-Alanine→N-(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanine→N-Hydroxysuccinimide→Ethyl 2-([(2S)-1-[(2,5-dioxopyrrolidin-1-yl)oxy]-1-oxopropan-2-yl]amino)-4-phenylbutanoate→N-(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl-4,5-ditritium-L-proline→(2Z)-But-2-enedioic acid N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-4,5-ditritium-L-proline
1-Bromo-5-chloropentane→Ethyl 2-ethoxy-2-oxoacetate→7-Chloro-2-oxoheptanoic acid ethyl ester→Ethyl 7-bromo-2-oxoheptanoate→Butyl 7-chloro-2-oxoheptanoate→2,2-Dimethylcyclopropane-1(S)-carboxamide→7-Chloro-2-[(1S)-2,2-dimethylcyclopropylcarboxamido]-2-heptenoic acid ethyl ester→Ethyl (2Z)-7-bromo-2-([[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino)hept-2-enoate→Butyl (2Z)-7-chloro-2-[[(1S)-2,2-dimethylcyclopropane-1-carbonyl]amino]hept-2-enoate→(2Z)-7-Chloro-2-([[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino)hept-2-enoic acid→(2Z)-7-Bromo-2-([[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino)hept-2-enoic acid→L-Cysteine→(2Z)-7-[[(2R)-2-Amino-2-carboxyethyl]sulfanyl]-2-([[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino)hept-2-enoic acid
cyclopentylmagnesium bromide→diethyl oxalate→ethyl 2-cyclopentyl-2-oxoacetate→phenylmagnesium bromide→ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-hydroxy-2-phenylacetic acid→(S)-1-phenylpropan-2-amine→(S)-1-phenylpropan-2-amine (R)-2-cyclopentyl-2-hydroxy-2-phenylacetate→(R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid→(R)-methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→(1R,5S,9s)-3-methyl-3-azabicyclo[3.3.1]nonan-9-ol
Intermediates available on this site
No listed intermediates for this target yet — send an RFQ directly and it will enter our matching pool.
This is a CAS-level registry record: registrations across routes are merged. Supplier offers and buyer demands will be matched on this CAS as the primary key.