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CAS 60-18-4
(-)-alpha-Amino-p-hydroxyhydrocinnamic acidL-tyrosine2(S)-Amino-3-(4-hydroxyphenyl)propionic acid(S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
Codes: Tamsulosin Hydrochloride-044, GADO-002, Atosiban-061, TIRO-015
Application context (from source-drug indications)
Erectile dysfunctionTadalafil/TamsulosinBenign prostatic hyperplasiaTadalafil/TamsulosinLower urinary tract symptomsSolifenacin Succinate/Tamsulosin HydrochlorideBenign prostatic hyperplasiaSolifenacin Succinate/Tamsulosin HydrochlorideOveractive bladderSolifenacin Succinate/Tamsulosin HydrochlorideDrug-related adverse effects and reactionsSolifenacin Succinate/Tamsulosin HydrochlorideBladder neck obstructionSolifenacin Succinate/Tamsulosin HydrochlorideBenign prostatic hyperplasiaDutasteride/Tamsulosin HydrochlorideBenign prostatic hyperplasiaTamsulosin HydrochlorideUrinary tract infectionTamsulosin HydrochlorideUrinary retentionTamsulosin HydrochlorideInguinal herniaTamsulosin HydrochlorideVoiding dysfunctionTamsulosin HydrochlorideLower urinary tract symptomsTamsulosin HydrochlorideContrast imagingGadoxetate DisodiumDiagnostic agentGadoxetate DisodiumProstate cancerGadoxetate DisodiumCastration-resistant prostate cancerGadoxetate DisodiumLiver cancerGadoxetate DisodiumHepatocellular carcinomaGadoxetate Disodium产科分娩（早产）Atosiban acetate早产（孕37周前）Atosiban acetateEndometriosisAtosiban acetateUnstable anginaTirofiban Hydrochloride HydrateMyocardial infarctionTirofiban Hydrochloride HydrateCoronary thrombosisTirofiban Hydrochloride HydrateAcute coronary syndromeTirofiban Hydrochloride HydrateThrombosisTirofiban Hydrochloride HydrateCerebral infarctionTirofiban Hydrochloride Hydrate
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Tadalafil/Tamsulosin | Tier C — Watch / trade | - |
| Solifenacin Succinate/Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Dutasteride/Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Gadoxetate Disodium | Tier C — Watch / trade | - |
| Atosiban acetate | Tier C — Watch / trade | - |
| Tirofiban Hydrochloride Hydrate | 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.
(-)-alpha-Amino-p-hydroxyhydrocinnamic acid→N-Acetyl-L-tyrosine→Ethyl N-acetyl-L-tyrosinate→Ethyl N-acetyl-O-methyl-L-tyrosinate→N-[(2S)-1-Hydroxy-3-(4-methoxyphenyl)propan-2-yl]acetamide→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→1-Methoxy-4-[(1E)-2-nitroprop-1-en-1-yl]benzene→N-Hydroxy-1-(4-methoxyphenyl)propan-2-imine→N-[(1E)-1-(4-Methoxyphenyl)prop-1-en-2-yl]acetamide→N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl 4-methylbenzenesulfonate→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-Hydroxy-2-ethoxybenzene→1-Chloro-2-hydroxyethane→2-(2-Ethoxyphenoxy)ethanol
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 14total yield: 2.091g(Tamsulosin Hydrochloride (API))
(-)-alpha-Amino-p-hydroxyhydrocinnamic acid→N-Acetyl-L-tyrosine→Ethyl N-acetyl-L-tyrosinate→Ethyl N-acetyl-O-methyl-L-tyrosinate→N-[(2S)-1-Hydroxy-3-(4-methoxyphenyl)propan-2-yl]acetamide→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→1-Methoxy-4-[(1E)-2-nitroprop-1-en-1-yl]benzene→N-Hydroxy-1-(4-methoxyphenyl)propan-2-imine→N-[(1E)-1-(4-Methoxyphenyl)prop-1-en-2-yl]acetamide→N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl 4-methylbenzenesulfonate→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-Hydroxy-2-ethoxybenzene→1-Chloro-2-hydroxyethane→2-(2-Ethoxyphenoxy)ethanol
Dutasteride/Tamsulosin HydrochlorideOptimised routesteps: 14total yield: 2.091g(Tamsulosin Hydrochloride (API))
(-)-alpha-Amino-p-hydroxyhydrocinnamic acid→N-Acetyl-L-tyrosine→Ethyl N-acetyl-L-tyrosinate→Ethyl N-acetyl-O-methyl-L-tyrosinate→N-[(2S)-1-Hydroxy-3-(4-methoxyphenyl)propan-2-yl]acetamide→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→1-Methoxy-4-[(1E)-2-nitroprop-1-en-1-yl]benzene→N-Hydroxy-1-(4-methoxyphenyl)propan-2-imine→N-[(1E)-1-(4-Methoxyphenyl)prop-1-en-2-yl]acetamide→N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl 4-methylbenzenesulfonate→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-Hydroxy-2-ethoxybenzene→1-Chloro-2-hydroxyethane→2-(2-Ethoxyphenoxy)ethanol
(-)-alpha-Amino-p-hydroxyhydrocinnamic acid→N-Acetyl-L-tyrosine→Ethyl N-acetyl-L-tyrosinate→Ethyl N-acetyl-O-methyl-L-tyrosinate→N-[(2S)-1-Hydroxy-3-(4-methoxyphenyl)propan-2-yl]acetamide→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→1-Methoxy-4-[(1E)-2-nitroprop-1-en-1-yl]benzene→N-Hydroxy-1-(4-methoxyphenyl)propan-2-imine→N-[(1E)-1-(4-Methoxyphenyl)prop-1-en-2-yl]acetamide→N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl 4-methylbenzenesulfonate→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-Hydroxy-2-ethoxybenzene→1-Chloro-2-hydroxyethane→2-(2-Ethoxyphenoxy)ethanol
L-tyrosine→(tert-butoxycarbonyl)-L-tyrosine→(S)-2-((tert-butoxycarbonyl)amino)-3-(4-ethoxyphenyl)propanoic acid→tert-butyl (S)-(1-(4-ethoxyphenyl)-3-hydroxypropan-2-yl)carbamate→(S)-2-((tert-butoxycarbonyl)amino)-3-(4-ethoxyphenyl)propyl methanesulfonate→tert-butyl (S)-(1-((2-aminoethyl)amino)-3-(4-ethoxyphenyl)propan-2-yl)carbamate→(S)-N1-(2-aminoethyl)-3-(4-ethoxyphenyl)propane-1,2-diamine hydrochloride→di-tert-butyl 2,2'-((2-((2-(bis(2-(tert-butoxy)-2-oxoethyl)amino)-3-(4-ethoxyphenyl)propyl)(2-(tert-butoxy)-2-oxoethyl)amino)ethyl)azanediyl)(S)-diacetate→Gadoxetate sodium
(S)-2-amino-3-(4-hydroxyphenyl)propanoic acid→butane-1-sulfonyl chloride hydrochloride→(S)-2-(butylsulfonamido)-3-(4-hydroxyphenyl)propanoic acid→TIRO-018→(S)-2-(butylsulfonamido)-3-(4-(4-(pyridin-4-yl)butoxy)phenyl)propanoic acid→(S)-2-(butylsulfonamido)-3-(4-(4-(piperidin-4-yl)butoxy)phenyl)propanoic acid→4-methylpyridine→1-bromo-3-chloropropane
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