CAS 147-85-3

(S)-pyrrolidine-2-carboxylic acid(-)-L-Proline<-fgf->L-Proline(S)-(-)-ProlineL-ProlinePyrrolidine-2(S)-carboxylic acid

Codes: IPRA-016, Enalapril-004, VILD-009, Atosiban-028, EPTI-025

Application context (from source-drug indications)

Type 2 diabetesSitagliptin Phosphate Monohydrate/Ipragliflozin L-ProlineCardiac and vascular disordersAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHypertensionAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHyperlipidaemiaAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHeart diseaseAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilEssential hypertensionEnalapril Maleate/Folic AcidType 2 diabetesVildagliptinSchizophreniaVildagliptinDyslipidaemiaVildagliptinInsulin resistanceVildagliptinType 1 diabetesVildagliptinDiabetesVildagliptinHeart failureEnalapril MaleateHypertensionEnalapril MaleateMyocardial infarctionEnalapril MaleateAngina pectorisEnalapril MaleateLeft ventricular dysfunctionEnalapril MaleateSolid tumourEnalapril MaleateType 2 diabetesIpragliflozin L-ProlineType 1 diabetesIpragliflozin L-ProlineDiabetesIpragliflozin L-ProlineLiver diseaseIpragliflozin L-Proline产科分娩（早产）Atosiban acetate早产（孕37周前）Atosiban acetateEndometriosisAtosiban acetateUnstable anginaEptifibatideMyocardial infarctionEptifibatideIschaemic strokeEptifibatideAcute coronary syndromeEptifibatideSickle cell diseaseEptifibatideST段抬高型心肌梗死Eptifibatide

Source drugs (routes using this intermediate)

Drug	Tier	Expiry
Sitagliptin Phosphate Monohydrate/Ipragliflozin L-Proline	Tier C — Watch / trade	-
Atorvastatin/Hydrochlorothiazide/Aspirin/Enalapril	Tier C — Watch / trade	-
Enalapril Maleate/Folic Acid	Tier C — Watch / trade	-
Vildagliptin	Tier B — Position early	-
Enalapril Maleate	Tier C — Watch / trade	-
Ipragliflozin L-Proline	Tier C — Watch / trade	-
Atosiban acetate	Tier C — Watch / trade	-
Eptifibatide	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.

Sitagliptin Phosphate Monohydrate/Ipragliflozin L-ProlineProcess routesteps: 8total yield: 1.7 g

5-bromo-2-fluorobenzaldehyde→benzo[b]thiophene→benzo[b]thiophen-2-yl(5-bromo-2-fluorophenyl)methanol→2-(5-bromo-2-fluorobenzyl)benzo[b]thiophene→2-((5-bromo-2-fluorophenyl)chloromethyl)benzo[b]thiophene→(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one→(2S,3R,4S,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol→(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate→(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate→(S)-pyrrolidine-2-carboxylic acid

Atorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilOptimised routesteps: 2total yield: 4.2g(Enalapril)

N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanine→(-)-L-Proline<-fgf->L-Proline→(S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline→trans-2-Butenedioic acid

Atorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilOptimised routesteps: 5total yield: 206.58g(Enalapril)

Pyrrolidine→Ethyl (2S)-2-[[(2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl]amino]-4-phenylbutanoate→Trimethylsilyl 1-(trimethylsilyl)-L-prolinate→Trimethylsilyl N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-L-prolinate→(S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline→N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine→(S)-(-)-Proline

Atorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilOptimised routesteps: 3total yield: 20.9g(Enalapril)

N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanine→(S)-(-)-Proline→(S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline

Atorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilOptimised routesteps: 8total yield: /

L-Alanine→N-Boc-2(S)-aminopropanoic acid→(4R)-4-Amino-1,3-oxazolidine-2,5-dione→Methyl L-prolinate hydrogen chloride→Methyl N-(tert-butoxycarbonyl)-L-alanyl-L-prolinate→N-(tert-Butoxycarbonyl)-L-alanyl-L-proline→L-Proline→L-Alanyl-L-proline→2-Oxo-4-phenylbutyric acid ethyl ester→(S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline

Enalapril Maleate/Folic AcidOptimised routesteps: 2total yield: 4.2g(Enalapril)

N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanine→(-)-L-Proline<-fgf->L-Proline→(S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline→trans-2-Butenedioic acid

Enalapril Maleate/Folic AcidOptimised routesteps: 5total yield: 206.58g(Enalapril)

Enalapril Maleate/Folic AcidOptimised routesteps: 3total yield: 20.9g(Enalapril)

N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanine→(S)-(-)-Proline→(S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline

Enalapril Maleate/Folic AcidOptimised routesteps: 8total yield: /

VildagliptinOptimised routesteps: 3total yield: /

2-chloroacetyl chloride→(S)-1-(2-chloroacetyl)pyrrolidine-2-carboxamide→(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile→(S)-pyrrolidine-2-carboxylic acid→(2-chloroacetyl)-L-proline

Enalapril MaleateOptimised routesteps: 2total yield: 4.2g(Enalapril)

N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanine→(-)-L-Proline<-fgf->L-Proline→(S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline→trans-2-Butenedioic acid

Enalapril MaleateOptimised routesteps: 5total yield: 206.58g(Enalapril)

Enalapril MaleateOptimised routesteps: 3total yield: 20.9g(Enalapril)

N-[1-Ethoxy-1-oxo-4-phenylbutan-2(S)-yl]-L-alanine→(S)-(-)-Proline→(S)-1-[N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline

Enalapril MaleateOptimised routesteps: 8total yield: /

Ipragliflozin L-ProlineProcess routesteps: 8total yield: 1.7 g

Atosiban acetateOptimised routesteps: 8total yield: /

S-Benzyl-N-(tert-butoxycarbonyl)-L-cysteine→1-Hydroxy-2,5-pyrrolidinedione→2,5-Dioxopyrrolidin-1-yl S-benzyl-N-(tert-butoxycarbonyl)-L-cysteinate→Pyrrolidine-2(S)-carboxylic acid→N2-(tert-Butoxycarbonyl)-L-asparaginyl-S-benzyl-L-cysteinyl-L-proline→S-Benzyl-N-(tert-butoxycarbonyl)-L-cysteinyl-L-proline→S-Benzyl-L-cysteinyl-L-proline→2,5-Dioxopyrrolidin-1-yl N2-(tert-butoxycarbonyl)-L-asparaginate→N2-(tert-Butoxycarbonyl)-L-asparagine→L-Asparaginyl-S-benzyl-L-cysteinyl-L-proline trifluoroacetate→2,5-Dioxopyrrolidin-1-yl O-benzyl-N-(tert-butoxycarbonyl)-L-threoninate→O-Benzyl-N-(tert-butoxycarbonyl)-L-threonine→O-Benzyl-N-(tert-butoxycarbonyl)-L-threonyl-L-asparaginyl-S-benzyl-L-cysteinyl-L-proline

Atosiban acetateOptimised routesteps: 8total yield: 118.85g(Atosiban-074)

2(S),4-Diamino-4-oxobutyric acid→N2-(Trifluoroacetyl)-L-asparagine→2,5-Dioxopyrrolidin-1-yl N2-(trifluoroacetyl)-L-asparaginate→(+)-S-Trityl-L-cysteine→2,5-Dioxopyrrolidin-1-yl N2-(trifluoroacetyl)-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolinate→N2-(Trifluoroacetyl)-L-asparaginyl-S-(triphenylmethyl)-L-cysteine→2,5-Dioxopyrrolidin-1-yl N2-(trifluoroacetyl)-L-asparaginyl-S-(triphenylmethyl)-L-cysteinate→N2-(Trifluoroacetyl)-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-proline→Nalpha-tert-Butoxycarbonyl-L-ornithine→N2-(Trifluoroacetyl)-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithine→2,5-Dioxopyrrolidin-1-yl N2-(trifluoroacetyl)-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithinate→(S)-(-)-Proline

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

Atosiban acetateOptimised routesteps: 3total yield: /

N-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-S-(triphenylmethyl)-L-cysteinyl-L-proline→Resin bound S-(triphenylmethyl)-L-cysteinyl-L-prolyl-N5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-ornithylglycinamide→Resin bound Orn(Dde)-Gly-NH→N-(9-Fluorenylmethoxycarbonyl)-S-trityl-L-cysteine→(S)-(-)-Proline

EptifibatideOptimised routesteps: 8total yield: 1.20 g

2-aminoacetic acid→methyl glycinate hydrochloride→(S)-2-(((benzyloxy)carbonyl)amino)-6-guanidinohexanoic acid→(S)-methyl 2-(2-amino-6-guanidinohexanamido)acetate→3-((acetamidomethyl)thio)propanoic acid→(S)-10-(4-guanidinobutyl)-2,8,11-trioxo-5-thia-3,9,12-triazatetradecan-14-oic acid→(S)-methyl 1-((S)-2-((S)-2-amino-4-(tert-butoxy)-4-oxobutanamido)-3-(1H-indol-3-yl)propanoyl)pyrrolidine-2-carboxylate→(S)-1-((10S,16S,19S)-19-((1H-indol-3-yl)methyl)-16-(2-(tert-butoxy)-2-oxoethyl)-10-(4-guanidinobutyl)-2,8,11,14,17-pentaoxo-5-thia-3,9,12,15,18-pentaazaicosan-20-oyl)pyrrolidine-2-carboxylic acid→(R)-3-((acetamidomethyl)thio)-2-aminopropanamide→(S)-pyrrolidine-2-carboxylic acid→methyl L-prolinate hydrochloride→(S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoic acid→(S)-methyl 1-((S)-2-amino-3-(1H-indol-3-yl)propanoyl)pyrrolidine-2-carboxylate→(S)-2-(((benzyloxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid

EptifibatideOptimised routesteps: 6total yield: /

N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid→3-(tritylthio)propanoic acid→(S)-pyrrolidine-2-carboxylic acid→(S)-tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(((S)-1-((S)-2-(((R)-1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-4-oxobutanoate→L-cysteine hydrochloride→(R)-(9H-fluoren-9-yl)methyl (1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamate→(2R,3R)-2,3-dihydroxysuccinic acid→(R)-2-amino-3-(tritylthio)propanamide (2R,3R)-2,3-dihydroxysuccinate→(R)-1-((S)-2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-3-(1H-indol-3-yl)propanoyl)pyrrolidine-2-carboxylic acid→EPTI-057→EPTI-058→(S)-2-amino-3-(1H-indol-3-yl)propanoic acid→(S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoic acid→3-bromoprop-1-ene→(R)-2-allyl 1-tert-butyl pyrrolidine-1,2-dicarboxylate→(R)-allyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoyl)pyrrolidine-2-carboxylate→(R)-allyl 1-((S)-2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-3-(1H-indol-3-yl)propanoyl)pyrrolidine-2-carboxylate→EPTI-065→EPTI-066→EPTI-067

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