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CAS 123-11-5
4-Methoxybenzaldehyde4-(Methyloxy)benzaldehyde
Codes: Tamsulosin Hydrochloride-021, (X)140605-22-a
Application context (from source-drug indications)
Erectile dysfunctionTadalafil/TamsulosinBenign prostatic hyperplasiaTadalafil/TamsulosinBladder cancerDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Head and neck cancerDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Head and neck squamous cell carcinomaDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Solid tumourDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Lower 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 HydrochlorideNon-small cell lung cancerDocetaxel （Beihai）Prostate cancerDocetaxel （Beihai）Castration-resistant prostate cancerDocetaxel （Beihai）Breast cancerDocetaxel （Beihai）Head and neck cancerDocetaxel （Beihai）Head and neck squamous cell carcinomaDocetaxel （Beihai）
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Tadalafil/Tamsulosin | Tier C — Watch / trade | - |
| Docetaxel polymeric micelle (Samyang Biopharmaceuticals) | 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 | - |
| Docetaxel （Beihai） | 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.
5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→Benzaldehyde→4-Methoxybenzaldehyde→4-Formylphenol→(4-Fluorophenyl)methanone→2-methoxy-5-[(2R)-2-[(E)-(phenylmethylidene)amino]propyl]benzene-1-sulfonamide→2-Methoxy-5-[(2R)-2-[(E)-[(4-methoxyphenyl)methylidene]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Hydroxyphenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Fluorophenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→1-ethoxy-2-(2-iodoethoxy)benzene→(E)-[2-(2-ethoxyphenoxy)ethyl][(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl](phenylmethylidene)azanium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-methoxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-hydroxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-fluorophenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
4-Methoxybenzaldehyde→2-Acetamidoacetic acid→(4E)-4-(4-Methoxybenzylidene)-2-methyl-1,3-oxazol-5(4H)-one→(2E)-2-(Acetylamino)-3-(4-methoxyphenyl)prop-2-enoic acid→N-Acetyl-O-methyl-L-tyrosine→O-Methyl-L-tyrosine→Ethyl O-methyl-L-tyrosinate→Ethyl N-[(benzyloxy)carbonyl]-O-methyl-L-tyrosinate→Benzyl [(2S)-1-hydroxy-3-(4-methoxyphenyl)propan-2-yl]carbamate→(2S)-2-[[(Benzyloxy)carbonyl]amino]-3-(4-methoxyphenyl)propyl 4-methylbenzenesulfonate→Benzyl [(2S)-1-iodo-3-(4-methoxyphenyl)propan-2-yl]carbamate→Benzyl [(2R)-1-(4-methoxyphenyl)propan-2-yl]carbamate
Benzaldehyde→1-Hydroxyacetone→(3R,4S)-3-Hydroxy-4-[(4-methoxyphenyl)amino]-4-phenylbutan-2-one→(4S,5R)-5-Acetyl-3-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidin-2-one→(4S,5R)-5-Acetyl-4-phenyl-1,3-oxazolidin-2-one→(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid→(2R,3S)-3-Phenylisoserine methyl ester→Bis(1,1-dimethylethyl) dicarbonoate→3(S)-(tert-Butoxycarbonylamino)-2(R)-hydroxy-3-phenylpropionic acid methyl ester→4-(Methyloxy)benzaldehyde→2-(4-Methoxyphenyl)-4(S)-phenyloxazolidine-3,5(R)-dicarboxylic acid 3-tert-butyl 5-methyl diester→(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid→Benzoic acid (2alpha,5beta,7beta,9beta,10beta,13alpha)-4,10-diacetoxy-1,9,13-trihydroxy-7-[methyl(diphenyl)silyloxy]-5,20-epoxytax-11-en-2-yl ester→2-(4-Methoxyphenyl)-4(S)-phenyloxazolidine-3,5(R)-dicarboxylic acid 3-tert-butyl 5-[(2aR,4S,4aR,5S,6R,9S,11S,12S,12aR,12bS)-6,12b-diacetoxy-12-(benzoyloxy)-5,11-dihydroxy-4a,8,13,13-tetramethyl-4-[methyl(diphenyl)silyloxy]-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-9-yl] diester
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 4total yield: 18g(Tamsulosin Hydrochloride (API))
5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→Benzaldehyde→4-Methoxybenzaldehyde→4-Formylphenol→(4-Fluorophenyl)methanone→2-methoxy-5-[(2R)-2-[(E)-(phenylmethylidene)amino]propyl]benzene-1-sulfonamide→2-Methoxy-5-[(2R)-2-[(E)-[(4-methoxyphenyl)methylidene]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Hydroxyphenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Fluorophenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→1-ethoxy-2-(2-iodoethoxy)benzene→(E)-[2-(2-ethoxyphenoxy)ethyl][(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl](phenylmethylidene)azanium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-methoxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-hydroxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-fluorophenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
4-Methoxybenzaldehyde→2-Acetamidoacetic acid→(4E)-4-(4-Methoxybenzylidene)-2-methyl-1,3-oxazol-5(4H)-one→(2E)-2-(Acetylamino)-3-(4-methoxyphenyl)prop-2-enoic acid→N-Acetyl-O-methyl-L-tyrosine→O-Methyl-L-tyrosine→Ethyl O-methyl-L-tyrosinate→Ethyl N-[(benzyloxy)carbonyl]-O-methyl-L-tyrosinate→Benzyl [(2S)-1-hydroxy-3-(4-methoxyphenyl)propan-2-yl]carbamate→(2S)-2-[[(Benzyloxy)carbonyl]amino]-3-(4-methoxyphenyl)propyl 4-methylbenzenesulfonate→Benzyl [(2S)-1-iodo-3-(4-methoxyphenyl)propan-2-yl]carbamate→Benzyl [(2R)-1-(4-methoxyphenyl)propan-2-yl]carbamate
Dutasteride/Tamsulosin HydrochlorideOptimised routesteps: 4total yield: 18g(Tamsulosin Hydrochloride (API))
5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→Benzaldehyde→4-Methoxybenzaldehyde→4-Formylphenol→(4-Fluorophenyl)methanone→2-methoxy-5-[(2R)-2-[(E)-(phenylmethylidene)amino]propyl]benzene-1-sulfonamide→2-Methoxy-5-[(2R)-2-[(E)-[(4-methoxyphenyl)methylidene]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Hydroxyphenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Fluorophenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→1-ethoxy-2-(2-iodoethoxy)benzene→(E)-[2-(2-ethoxyphenoxy)ethyl][(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl](phenylmethylidene)azanium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-methoxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-hydroxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-fluorophenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
4-Methoxybenzaldehyde→2-Acetamidoacetic acid→(4E)-4-(4-Methoxybenzylidene)-2-methyl-1,3-oxazol-5(4H)-one→(2E)-2-(Acetylamino)-3-(4-methoxyphenyl)prop-2-enoic acid→N-Acetyl-O-methyl-L-tyrosine→O-Methyl-L-tyrosine→Ethyl O-methyl-L-tyrosinate→Ethyl N-[(benzyloxy)carbonyl]-O-methyl-L-tyrosinate→Benzyl [(2S)-1-hydroxy-3-(4-methoxyphenyl)propan-2-yl]carbamate→(2S)-2-[[(Benzyloxy)carbonyl]amino]-3-(4-methoxyphenyl)propyl 4-methylbenzenesulfonate→Benzyl [(2S)-1-iodo-3-(4-methoxyphenyl)propan-2-yl]carbamate→Benzyl [(2R)-1-(4-methoxyphenyl)propan-2-yl]carbamate
5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→Benzaldehyde→4-Methoxybenzaldehyde→4-Formylphenol→(4-Fluorophenyl)methanone→2-methoxy-5-[(2R)-2-[(E)-(phenylmethylidene)amino]propyl]benzene-1-sulfonamide→2-Methoxy-5-[(2R)-2-[(E)-[(4-methoxyphenyl)methylidene]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Hydroxyphenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Fluorophenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→1-ethoxy-2-(2-iodoethoxy)benzene→(E)-[2-(2-ethoxyphenoxy)ethyl][(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl](phenylmethylidene)azanium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-methoxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-hydroxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-fluorophenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
4-Methoxybenzaldehyde→2-Acetamidoacetic acid→(4E)-4-(4-Methoxybenzylidene)-2-methyl-1,3-oxazol-5(4H)-one→(2E)-2-(Acetylamino)-3-(4-methoxyphenyl)prop-2-enoic acid→N-Acetyl-O-methyl-L-tyrosine→O-Methyl-L-tyrosine→Ethyl O-methyl-L-tyrosinate→Ethyl N-[(benzyloxy)carbonyl]-O-methyl-L-tyrosinate→Benzyl [(2S)-1-hydroxy-3-(4-methoxyphenyl)propan-2-yl]carbamate→(2S)-2-[[(Benzyloxy)carbonyl]amino]-3-(4-methoxyphenyl)propyl 4-methylbenzenesulfonate→Benzyl [(2S)-1-iodo-3-(4-methoxyphenyl)propan-2-yl]carbamate→Benzyl [(2R)-1-(4-methoxyphenyl)propan-2-yl]carbamate
Benzaldehyde→1-Hydroxyacetone→(3R,4S)-3-Hydroxy-4-[(4-methoxyphenyl)amino]-4-phenylbutan-2-one→(4S,5R)-5-Acetyl-3-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidin-2-one→(4S,5R)-5-Acetyl-4-phenyl-1,3-oxazolidin-2-one→(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid→(2R,3S)-3-Phenylisoserine methyl ester→Bis(1,1-dimethylethyl) dicarbonoate→3(S)-(tert-Butoxycarbonylamino)-2(R)-hydroxy-3-phenylpropionic acid methyl ester→4-(Methyloxy)benzaldehyde→2-(4-Methoxyphenyl)-4(S)-phenyloxazolidine-3,5(R)-dicarboxylic acid 3-tert-butyl 5-methyl diester→(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid→Benzoic acid (2alpha,5beta,7beta,9beta,10beta,13alpha)-4,10-diacetoxy-1,9,13-trihydroxy-7-[methyl(diphenyl)silyloxy]-5,20-epoxytax-11-en-2-yl ester→2-(4-Methoxyphenyl)-4(S)-phenyloxazolidine-3,5(R)-dicarboxylic acid 3-tert-butyl 5-[(2aR,4S,4aR,5S,6R,9S,11S,12S,12aR,12bS)-6,12b-diacetoxy-12-(benzoyloxy)-5,11-dihydroxy-4a,8,13,13-tetramethyl-4-[methyl(diphenyl)silyloxy]-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-9-yl] diester
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