CAS 15761-39-4

(S)-1-(tert-Butoxycarbonyl)pyrrolidine-2-carboxylic acidN-Boc-L-proline(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Codes: Tamsulosin Hydrochloride-087, Emitasvir Phosphate-002, RAVI-005, Atosiban-133

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 HydrochlorideHepatitis CEmitasvir PhosphateRenal impairmentEmitasvir PhosphateHepatic function declineEmitasvir PhosphateChronic hepatitis CEmitasvir PhosphateHepatitis CRavidasvir HydrochlorideViral infectionRavidasvir HydrochlorideChronic hepatitis CRavidasvir Hydrochloride产科分娩（早产）Atosiban acetate早产（孕37周前）Atosiban acetateEndometriosisAtosiban acetate

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	-
Emitasvir Phosphate	Tier C — Watch / trade	-
Ravidasvir Hydrochloride	Tier C — Watch / trade	-
Atosiban acetate	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.

Tadalafil/TamsulosinOptimised routesteps: 6total yield: /

5-Acetyl-2-methoxybenzene-1-sulfonamide→2-(2-Ethoxyphenoxy)ethylamine→Tamsulosin Hydrochloride-085→(2R)-Hydroxy(phenyl)acetic acid 5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzene-1-sulfonamide→(S)-1-(tert-Butoxycarbonyl)pyrrolidine-2-carboxylic acid→Carbonochloridic acid ethyl ester→Ethoxycarbonyl 1-(tert-butoxycarbonyl)-L-prolinate→2-Methoxydibenzo[b,d]furan-3-amine→tert-Butyl (2S)-2-[(2-methoxydibenzo[b,d]furan-3-yl)carbamoyl]pyrrolidine-1-carboxylate→N-(2-Methoxydibenzo[b,d]furan-3-yl)-L-prolinamide

Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 6total yield: /

Dutasteride/Tamsulosin HydrochlorideOptimised routesteps: 6total yield: /

Tamsulosin HydrochlorideOptimised routesteps: 6total yield: /

Emitasvir PhosphateOptimised routesteps: 6total yield: 230.40mg(Emitasvir Phosphate (API))

2-Amino-4-bromophenylamine→N-Boc-L-proline→tert-Butyl 2(S)-(5-bromo-2-benzimidazolyl)pyrrolidine-1-carboxylate→tert-Butyl (2S)-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]pyrrolidine-1-carboxylate→tert-Butyl (2S)-2-[4-(4-[(1S,4R)-8-[(trifluoromethanesulfonyl)oxy]-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]phenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate→tert-Butyl (2S)-2-(4-[4-[(1S,4R)-8-[2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1H-benzimidazol-5-yl]-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]phenyl]-1H-imidazol-2-yl)pyrrolidine-1-carboxyla te→2-[(2S)-Pyrrolidin-2-yl]-5-[(1R,4S)-8-(4-[2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-4-yl]phenyl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-benzimidazole→2-[(2S)-Pyrrolidin-2-yl]-5-[(1R,4S)-8-(4-[2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-benzimidazole tetrahydrogen chloride→N-(Methoxycarbonyl)-L-valine→Methyl [(2S)-1-[(2S)-2-[5-[(1R,4S)-8-(4-[2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-4-yl]phenyl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-benzimi dazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate

Emitasvir PhosphateOptimised routesteps: 10total yield: 697mg(Emitasvir Phosphate-005)

N-Boc-L-proline→tert-Butyl (2S)-2-[4-(4-[(1S,4R)-8-[(trifluoromethanesulfonyl)oxy]-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]phenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate→1-Acetyl-4-bromobenzene→4'-Bromophenacyl bromide→2-[2-(4-Bromophenyl)-2-oxoethyl] 1-tert-butyl (2S)-pyrrolidine-1,2-dicarboxylate→(S)-tert-Butyl 2-(5-(4-bromophenyl)-1h-imidazol-2-yl)pyrrolidine-1-carboxylate→tert-Butyl (2S)-2-[4-[4-(3,3,4,4-tetramethylborolan-1-yl)phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carboxylate→1,2,3,4-Tetrahydro-1,4-methanonaphthalene-5,8-diyl bis(trifluoromethanesulfonate)→tert-Butyl (2S)-2-[4-(4-[8-[(trifluoromethanesulfonyl)oxy]-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]phenyl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate→Quinone→Cyclopenta-1,3-diene→Tricyclo[6.2.1.0,2,7]undeca-4,9-diene-3,6-dione→1,4-Dihydro-1,4-methanonaphthalene-5,8-diol→1,2,3,4-Tetrahydro-1,4-methanonaphthalene-5,8-diol

Ravidasvir HydrochlorideOriginator routesteps: 12total yield: 0.039 g

6-bromo-2-naphthoic acid→RAVI-002→RAVI-003→RAVI-004→(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid→RAVI-006→RAVI-007→RAVI-008→(methoxycarbonyl)-D-valine→RAVI-010→4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)→RAVI-012→RAVI-013→4-bromobenzene-1,2-diamine→RAVI-015→RAVI-016

Atosiban acetateOptimised routesteps: 4total yield: /

S-(Acetamidomethyl)-N-(tert-butoxycarbonyl)-L-cysteine→N-Boc-L-proline→1-tert-Butyl 2-prop-2-en-1-yl (2S)-pyrrolidine-1,2-dicarboxylate→Prop-2-en-1-yl S-(acetamidomethyl)-N-(tert-butoxycarbonyl)-L-cysteinyl-L-prolinate→Pyrrolidine-2(S)-carboxylic acid

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