Routes are ordered originator first, then optimised / process (non-patent) routes; each lists steps, overall yield and the intermediate table (code / CAS / name) — ready for supplier sourcing and RFQ. Rendered by this site from structured data; no third-party route graphics used.
OptimisedRoute 1Steps 1 · Total yield /
Enalapril-00164920-29-2→Enalapril-00213485-59-1→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-001 | 64920-29-2 | Ethyl 2-oxo-4-phenylbutyrate |
| Enalapril-002 | 13485-59-1 | L-Alanyl-L-proline |
OptimisedRoute 2Steps 2 · Total yield 4.2g(Enalapril)
Enalapril-00382717-96-2→Enalapril-004147-85-3→Enalapril-00575847-73-3→Enalapril-006110-17-8→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-003 | 82717-96-2 | N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanine |
| Enalapril-004 | 147-85-3 | (-)-L-Proline<-fgf->L-Proline |
| Enalapril-005 | 75847-73-3 | (S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline |
| Enalapril-006 | 110-17-8Available | trans-2-Butenedioic acid |
OptimisedRoute 3Steps 9 · Total yield /
Enalapril-00753279-92-8→Enalapril-008120999-41-9→Enalapril-009138566-24-2→Enalapril-010—→Enalapril-0111142-20-7→Enalapril-01290315-82-5→Enalapril-01388767-98-0→Enalapril-01429375-30-2→Enalapril-015108428-39-3→Enalapril-0162812-46-6→Enalapril-01727544-35-0→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-007 | 53279-92-8 | 2-Hydroxy-4-phenylbutanenitrile |
| Enalapril-008 | 120999-41-9 | 2(R)-Hydroxy-4-phenylbutanenitrile |
| Enalapril-009 | 138566-24-2 | 4-Phenyl-2(R)-(tetrahydropyran-2-yloxy)butanenitrile |
| Enalapril-010 | - | 4-Phenyl-2(R)-(tetrahydropyran-2-yloxy)butyric acid |
| Enalapril-011 | 1142-20-7 | N-[(Benzyloxy)carbonyl]-L-alanine |
| Enalapril-012 | 90315-82-5 | Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate |
| Enalapril-013 | 88767-98-0 | 4-Phenyl-2(R)-(trifluoromethylsulfonyloxy)butyric acid ethyl ester |
| Enalapril-014 | 29375-30-2 | L-Alanyl-L-proline tert-butyl ester |
| Enalapril-015 | 108428-39-3 | N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanyl-L-proline tert-butyl ester |
| Enalapril-016 | 2812-46-6 | N-Boc-proline |
| Enalapril-017 | 27544-35-0 | N-(Benzyloxycarbonyl)-L-alanyl-L-proline tert-butyl ester |
OptimisedRoute 4Steps 4 · Total yield 4.11g(Enalapril)
Enalapril-01880828-26-8→Enalapril-019103377-40-8→Enalapril-02016652-71-4→Enalapril-021120924-94-9→Enalapril-00382717-96-2→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-018 | 80828-26-8 | N-[(2S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanine hydrochloride |
| Enalapril-019 | 103377-40-8 | Ethyl (2S)-2-[[(2S)-1-chloro-1-oxopropan-2-yl]amino]-4-phenylbutanoate |
| Enalapril-020 | 16652-71-4 | Benzyl L-prolinate hydrochloride |
| Enalapril-021 | 120924-94-9 | Benzyl N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-L-prolinate |
| Enalapril-003 | 82717-96-2 | N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanine |
OptimisedRoute 5Steps 1 · Total yield /
Enalapril-02288098-09-3→Enalapril-00575847-73-3→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-022 | 88098-09-3 | N-[(2S)-1-Ethoxy-1,4-dioxo-4-phenylbutan-2-yl]-L-alanyl-L-proline |
| Enalapril-005 | 75847-73-3 | (S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline |
OptimisedRoute 6Steps 6 · Total yield 174mg(Enalapril-033)
Enalapril-023103-63-9→Enalapril-0243277-89-2→Enalapril-02595-92-1→Enalapril-02664920-29-2→Enalapril-027108607-75-6→Enalapril-02856-41-7→Enalapril-029877932-98-4→Enalapril-0306066-82-6→Enalapril-031—→Enalapril-032—→Enalapril-033—→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-023 | 103-63-9 | (2-Bromoethyl)benzene |
| Enalapril-024 | 3277-89-2 | Bromido(2-phenylethyl)magnesium |
| Enalapril-025 | 95-92-1 | Oxalic acid diethyl diester |
| Enalapril-026 | 64920-29-2 | 2-Oxo-4-phenylbutyric acid ethyl ester |
| Enalapril-027 | 108607-75-6 | 4,5-Ditritium-L-proline |
| Enalapril-028 | 56-41-7 | L-Alanine |
| Enalapril-029 | 877932-98-4 | N-(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanine |
| Enalapril-030 | 6066-82-6 | N-Hydroxysuccinimide |
| Enalapril-031 | - | Ethyl 2-([(2S)-1-[(2,5-dioxopyrrolidin-1-yl)oxy]-1-oxopropan-2-yl]amino)-4-phenylbutanoate |
| Enalapril-032 | - | N-(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl-4,5-ditritium-L-proline |
| Enalapril-033 | - | (2Z)-But-2-enedioic acid N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-4,5-ditritium-L-proline |
OptimisedRoute 7Steps 11 · Total yield /
Enalapril-03415186-48-8→Enalapril-03510065-72-2→Enalapril-0361411634-44-0→Enalapril-03719810-31-2→Enalapril-0381100-88-5→Enalapril-039533931-02-1→Enalapril-040533931-01-0→Enalapril-041533931-03-2→Enalapril-04216721-45-2→Enalapril-043—→Enalapril-044—→Enalapril-04541324-66-7→Enalapril-046533931-05-4→Enalapril-047533931-06-5→Enalapril-0481516-08-1,64-17-5→Enalapril-00575847-73-3→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-034 | 15186-48-8Available | 2,2-Dimethyl-1,3-dioxolane-4(R)-carbaldehyde |
| Enalapril-035 | 10065-72-2 | L-Alanine methyl ester |
| Enalapril-036 | 1411634-44-0 | Methyl (Z)-N-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene]-L-alaninate |
| Enalapril-037 | 19810-31-2 | Benzyloxyacetyl chloride |
| Enalapril-038 | 1100-88-5 | Triphenyl(phenylmethyl)phosphonium chloride |
| Enalapril-039 | 533931-02-1 | Methyl (2S)-2-[(2S,3R)-3-(benzyloxy)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-oxoazetidin-1-yl]propanoate |
| Enalapril-040 | 533931-01-0 | Methyl (2S)-2-[(2S,3R)-3-(benzyloxy)-2-[(1S)-1,2-dihydroxyethyl]-4-oxoazetidin-1-yl]propanoate |
| Enalapril-041 | 533931-03-2 | Methyl (2S)-2-[(2R,3R)-3-(benzyloxy)-2-formyl-4-oxoazetidin-1-yl]propanoate |
| Enalapril-042 | 16721-45-2 | Benzylidene(triphenyl)-lambda5-phosphane |
| Enalapril-043 | - | Methyl (2S)-2-[(3R,4S)-3-(benzyloxy)-2-oxo-4-[(E)-2-phenylethenyl]azetidin-1-yl]propanoate |
| Enalapril-044 | - | (2S)-2-[(3R,4S)-3-Hydroxy-2-oxo-4-(2-phenylethyl)azetidin-1-yl]propanoic acid |
| Enalapril-045 | 41324-66-7 | Benzyl L-prolinate |
| Enalapril-046 | 533931-05-4 | Benzyl 1-[(2S)-2-[(3R,4S)-3-hydroxy-2-oxo-4-(2-phenylethyl)azetidin-1-yl]propanoyl]-L-prolinate |
| Enalapril-047 | 533931-06-5 | Benzyl 1-[(2S)-2-[(4S)-2,5-dioxo-4-(2-phenylethyl)-1,3-oxazolidin-3-yl]propanoyl]-L-prolinate |
| Enalapril-048 | 1516-08-1,64-17-5 | Ethyl alcohol |
| Enalapril-005 | 75847-73-3 | (S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline |
OptimisedRoute 8Steps 4 · Total yield 3.28g(Enalapril-054)
Enalapril-049100-52-7→Enalapril-050127-17-3→Enalapril-051—→Enalapril-052128573-54-6→Enalapril-05329678-81-7→Enalapril-05490315-82-5→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-049 | 100-52-7Available | Bitter almond |
| Enalapril-050 | 127-17-3 | 2-Oxopropionic acid |
| Enalapril-051 | - | Potassium (3E)-2-oxo-4-phenylbut-3-enoate |
| Enalapril-052 | 128573-54-6 | (2R,3E)-2-Hydroxy-4-phenylbut-3-enoic acid |
| Enalapril-053 | 29678-81-7 | 2(R)-Hydroxy-4-phenylbutyric acid |
| Enalapril-054 | 90315-82-5 | Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate |
OptimisedRoute 9Steps 7 · Total yield /
Enalapril-05517451-19-3→Enalapril-05675-64-9→Enalapril-05710017-37-5→Enalapril-0581190946-81-6→Enalapril-059586396-58-9→Enalapril-060586396-61-4→Enalapril-061115016-95-0→Enalapril-062125639-64-7→Enalapril-049100-52-7→Enalapril-050127-17-3→Enalapril-0481516-08-1,64-17-5→API · Enalapril Maleate
OptimisedRoute 10Steps 5 · Total yield 206.58g(Enalapril)
Enalapril-063123-75-1→Enalapril-0642252296-25-4→Enalapril-0657364-47-8→Enalapril-066273750-74-6→Enalapril-00575847-73-3→Enalapril-00382717-96-2→Enalapril-004147-85-3→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-063 | 123-75-1 | Pyrrolidine |
| Enalapril-064 | 2252296-25-4 | Ethyl (2S)-2-[[(2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl]amino]-4-phenylbutanoate |
| Enalapril-065 | 7364-47-8 | Trimethylsilyl 1-(trimethylsilyl)-L-prolinate |
| Enalapril-066 | 273750-74-6 | Trimethylsilyl N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-L-prolinate |
| Enalapril-005 | 75847-73-3 | (S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline |
| Enalapril-003 | 82717-96-2 | N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine |
| Enalapril-004 | 147-85-3 | (S)-(-)-Proline |
OptimisedRoute 11Steps 3 · Total yield 20.9g(Enalapril)
Enalapril-00382717-96-2→Enalapril-004147-85-3→Enalapril-00575847-73-3→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-003 | 82717-96-2 | N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanine |
| Enalapril-004 | 147-85-3 | (S)-(-)-Proline |
| Enalapril-005 | 75847-73-3 | (S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline |
OptimisedRoute 12Steps 5 · Total yield 3.9g(Enalapril-073)
Enalapril-06756-84-8→Enalapril-06832213-95-9→Enalapril-069116393-72-7→Enalapril-070100-39-0→Enalapril-071885357-46-0→Enalapril-072871123-99-8→Enalapril-073943-73-7→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-067 | 56-84-8 | (S)-Aminobutanedioic acid |
| Enalapril-068 | 32213-95-9 | Dimethyl L-aspartate hydrogen chloride |
| Enalapril-069 | 116393-72-7 | Dimethyl N-(triphenylmethyl)-L-aspartate |
| Enalapril-070 | 100-39-0 | 1-(Bromomethyl)benzene |
| Enalapril-071 | 885357-46-0 | Dimethyl 3-benzyl-N-(triphenylmethyl)-L-aspartate |
| Enalapril-072 | 871123-99-8 | (3R)-3-Benzyl-L-aspartic acid |
| Enalapril-073 | 943-73-7 | 2(S)-Amino-4-phenylbutanoic acid |
OptimisedRoute 13Steps 8 · Total yield /
Enalapril-07456-41-7→Enalapril-07515761-38-3→Enalapril-076—→Enalapril-0772133-40-6→Enalapril-07833300-71-9→Enalapril-07933300-72-0→Enalapril-004147-85-3→Enalapril-00213485-59-1→Enalapril-02664920-29-2→Enalapril-00575847-73-3→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-074 | 56-41-7 | L-Alanine |
| Enalapril-075 | 15761-38-3 | N-Boc-2(S)-aminopropanoic acid |
| Enalapril-076 | - | (4R)-4-Amino-1,3-oxazolidine-2,5-dione |
| Enalapril-077 | 2133-40-6 | Methyl L-prolinate hydrogen chloride |
| Enalapril-078 | 33300-71-9 | Methyl N-(tert-butoxycarbonyl)-L-alanyl-L-prolinate |
| Enalapril-079 | 33300-72-0 | N-(tert-Butoxycarbonyl)-L-alanyl-L-proline |
| Enalapril-004 | 147-85-3 | L-Proline |
| Enalapril-002 | 13485-59-1 | L-Alanyl-L-proline |
| Enalapril-026 | 64920-29-2 | 2-Oxo-4-phenylbutyric acid ethyl ester |
| Enalapril-005 | 75847-73-3 | (S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline |
OptimisedRoute 14Steps 3 · Total yield 37.9g(Enalapril-054)
Enalapril-080104-53-0→Enalapril-081—→Enalapril-008120999-41-9→Enalapril-05490315-82-5→API · Enalapril Maleate
| Code | CAS No. | Intermediate |
|---|
| Enalapril-080 | 104-53-0 | 3-Phenylpropionaldehyde |
| Enalapril-081 | - | Ethyl 2-oxo-4-phenylbut-3-enoate |
| Enalapril-008 | 120999-41-9 | 2(R)-Hydroxy-4-phenylbutanenitrile |
| Enalapril-054 | 90315-82-5 | Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate |