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CAS 90315-82-5
Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate
Codes: Enalapril-012, Enalapril-054
Application context (from source-drug indications)
Cardiac and vascular disordersAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHypertensionAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHyperlipidaemiaAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHeart diseaseAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilEssential hypertensionEnalapril Maleate/Folic AcidHeart failureEnalapril MaleateHypertensionEnalapril MaleateMyocardial infarctionEnalapril MaleateAngina pectorisEnalapril MaleateLeft ventricular dysfunctionEnalapril MaleateSolid tumourEnalapril Maleate
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Atorvastatin/Hydrochlorothiazide/Aspirin/Enalapril | Tier C — Watch / trade | - |
| Enalapril Maleate/Folic Acid | Tier C — Watch / trade | - |
| Enalapril Maleate | 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.
2-Hydroxy-4-phenylbutanenitrile→2(R)-Hydroxy-4-phenylbutanenitrile→4-Phenyl-2(R)-(tetrahydropyran-2-yloxy)butanenitrile→4-Phenyl-2(R)-(tetrahydropyran-2-yloxy)butyric acid→N-[(Benzyloxy)carbonyl]-L-alanine→Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate→4-Phenyl-2(R)-(trifluoromethylsulfonyloxy)butyric acid ethyl ester→L-Alanyl-L-proline tert-butyl ester→N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanyl-L-proline tert-butyl ester→N-Boc-proline→N-(Benzyloxycarbonyl)-L-alanyl-L-proline tert-butyl ester
Atorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilOptimised routesteps: 4total yield: 3.28g(Enalapril-054)
Bitter almond→2-Oxopropionic acid→Potassium (3E)-2-oxo-4-phenylbut-3-enoate→(2R,3E)-2-Hydroxy-4-phenylbut-3-enoic acid→2(R)-Hydroxy-4-phenylbutyric acid→Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate
Atorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilOptimised routesteps: 3total yield: 37.9g(Enalapril-054)
3-Phenylpropionaldehyde→Ethyl 2-oxo-4-phenylbut-3-enoate→2(R)-Hydroxy-4-phenylbutanenitrile→Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate
2-Hydroxy-4-phenylbutanenitrile→2(R)-Hydroxy-4-phenylbutanenitrile→4-Phenyl-2(R)-(tetrahydropyran-2-yloxy)butanenitrile→4-Phenyl-2(R)-(tetrahydropyran-2-yloxy)butyric acid→N-[(Benzyloxy)carbonyl]-L-alanine→Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate→4-Phenyl-2(R)-(trifluoromethylsulfonyloxy)butyric acid ethyl ester→L-Alanyl-L-proline tert-butyl ester→N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanyl-L-proline tert-butyl ester→N-Boc-proline→N-(Benzyloxycarbonyl)-L-alanyl-L-proline tert-butyl ester
Bitter almond→2-Oxopropionic acid→Potassium (3E)-2-oxo-4-phenylbut-3-enoate→(2R,3E)-2-Hydroxy-4-phenylbut-3-enoic acid→2(R)-Hydroxy-4-phenylbutyric acid→Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate
3-Phenylpropionaldehyde→Ethyl 2-oxo-4-phenylbut-3-enoate→2(R)-Hydroxy-4-phenylbutanenitrile→Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate
2-Hydroxy-4-phenylbutanenitrile→2(R)-Hydroxy-4-phenylbutanenitrile→4-Phenyl-2(R)-(tetrahydropyran-2-yloxy)butanenitrile→4-Phenyl-2(R)-(tetrahydropyran-2-yloxy)butyric acid→N-[(Benzyloxy)carbonyl]-L-alanine→Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate→4-Phenyl-2(R)-(trifluoromethylsulfonyloxy)butyric acid ethyl ester→L-Alanyl-L-proline tert-butyl ester→N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanyl-L-proline tert-butyl ester→N-Boc-proline→N-(Benzyloxycarbonyl)-L-alanyl-L-proline tert-butyl ester
Bitter almond→2-Oxopropionic acid→Potassium (3E)-2-oxo-4-phenylbut-3-enoate→(2R,3E)-2-Hydroxy-4-phenylbut-3-enoic acid→2(R)-Hydroxy-4-phenylbutyric acid→Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate
3-Phenylpropionaldehyde→Ethyl 2-oxo-4-phenylbut-3-enoate→2(R)-Hydroxy-4-phenylbutanenitrile→Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate
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