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CAS 71989-31-6

(((9H-fluoren-9-yl)methoxy)carbonyl)-L-prolineN-(9-Fluorenylmethoxycarbonyl)-L-prolineN-(9-Fluorenylmethoxycarbonyl)-L-proline<-fgf->1-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-proline

Codes: BATIF-004, Atosiban-007, EPTI-003

Application context (from source-drug indications)

Acute coronary syndromeBevifibatide CitrateUnstable anginaBevifibatide Citrate非ST段抬高型心肌梗死Bevifibatide CitrateIschaemic heart diseaseBevifibatide CitrateMyocardial infarctionBevifibatide CitrateAngina pectorisBevifibatide Citrate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)

DrugTierExpiry
Bevifibatide CitrateTier C — Watch / trade-
Atosiban acetateTier C — Watch / trade-
EptifibatideTier 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.

Bevifibatide CitrateOriginator routesteps: 9total yield: /
BATIF-001→N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine→(9H-fluoren-9-yl)methyl (R)-(1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamate→(((9H-fluoren-9-yl)methoxy)carbonyl)-L-proline→(9H-fluoren-9-yl)methyl (S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidine-1-carboxylate→Na-(((9H-fluoren-9-yl)methoxy)carbonyl)-1-(tert-butoxycarbonyl)-L-tryptophan→tert-butyl 3-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-oxopropyl)-1H-indole-1-carboxylate→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid→tert-butyl 3-((S)-2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-3-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-oxopropyl)-1H-indole-1-carboxylate→(((9H-fluoren-9-yl)methoxy)carbonyl)glycine→tert-butyl 3-((8S,11S)-8-(2-(tert-butoxy)-2-oxoethyl)-1-(9H-fluoren-9-yl)-11-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidine-1-carbonyl)-3,6,9-trioxo-2-oxa-4,7,10-triazadodecan-12-yl)-1H-indole-1-carboxylate→N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-Nw-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)-L-arginine→tert-butyl 3-((5S,11S,14S)-11-(2-(tert-butoxy)-2-oxoethyl)-1-(9H-fluoren-9-yl)-14-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidine-1-carbonyl)-3,6,9,12-tetraoxo-5-(3-(3-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)guanidino)propyl)-2-oxa-4,7,10,13-tetraazapentadecan-15-yl)-1H-indole-1-carboxylate→3-mercaptopropanoic acid→tert-butyl 3-((6S,12S,15S)-12-(2-(tert-butoxy)-2-oxoethyl)-1-imino-6-(3-mercaptopropanamido)-15-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidine-1-carbonyl)-7,10,13-trioxo-1-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran)-5-sulfonamido)-2,8,11,14-tetraazahexadecan-16-yl)-1H-indole-1-carboxylate→(S)-4-(((S)-1-((S)-2-(((R)-1-amino-3-mercapto-1-oxopropan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-3-(2-((S)-5-guanidino-2-(3-mercaptopropanamido)pentanamido)acetamido)-4-oxobutanoic acid
Atosiban acetateOptimised routesteps: 7total yield: 104.16g(Atosiban-013)
N-(9H-Fluoren-9-ylmethoxycarbonyl)glycine→Resin bound 9H-fluoren-9-ylmethyl (2-amino-2-oxoethyl)carbamate→Resin bound glycinamide→Fmoc-Orn(Boc)-OH→Resin bound S-trityl-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycinamide→Resin bound N5-(tert-butoxycarbonyl)-L-ornithylglycinamide→N-(9-Fluorenylmethoxycarbonyl)-L-proline→Resin bound L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycinamide→N-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-S-(triphenylmethyl)-L-cysteine→N2-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-N-(triphenylmethyl)-L-asparagine→Resin bound N-trityl-L-asparaginyl-S-trityl-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycinamide→O-tert-Butyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine→Resin bound O-tert-butyl-L-threonyl-N-trityl-L-asparaginyl-S-trityl-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycinamide
Atosiban acetateOptimised routesteps: 5total yield: 286g(Atosiban-097)
Resin bound glycine→CTC resin bound N5-(tert-butoxycarbonyl)-L-ornithylglycine→CTC resin bound L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycine→S-(Acetamidomethyl)-N-[[(9H-fluoren-9-yl)methoxy]carbonyl]-L-cysteine→CTC resin bouond S-(triphenylmethyl)-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycine→CTC resin bound N-(triphenylmethyl)-L-asparaginyl-S-(acetamidomethyl)-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycine→N-(9H-Fluoren-9-ylmethoxycarbonyl)glycine→N5-(tert-Butoxycarbonyl)-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-ornithine→N-(9-Fluorenylmethoxycarbonyl)-L-proline→Nalpha-(9-Fluorenylmethoxycarbonyl)-Ngamma-trityl-L-asparagine
Atosiban acetateOptimised routesteps: 9total yield: /
1-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithine→Glycinamide→Resin bound S-(triphenylmethyl)-L-cysteinyl-L-prolyl-L-ornithylglycinamide→1-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycinamide→1-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-L-prolyl-L-ornithylglycinamide→Resin bound L-prolyl-L-ornithylglycinamide→N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-asparagine→Resin bound L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-L-ornithylglycinamide→N-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-L-threonine→Resin bound L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-L-ornithylglycinamide→N-(9-Fluorenylmethoxycarbonyl)-L-proline<-fgf->1-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-proline→N5-(tert-Butoxycarbonyl)-L-ornithine<-fgf->Nalpha-tert-Butoxycarbonyl-L-ornithine<-fgf->Nalpha-Boc-L-ornithine<-fgf->N2-Boc-L-ornithine<-fgf->(2S)-5-Amino-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid→N-(9-Fluorenylmethoxycarbonyl)-S-trityl-L-cysteine<-fgf->N-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-S-(triphenylmethyl)-L-cysteine
Atosiban acetateOptimised routesteps: 7total yield: /
Resin bound 9H-fluoren-9-ylmethyl (2-amino-2-oxoethyl)carbamate→Resin bound Gly-NH→N5-[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)ethyl]-N2-[[(9H-fluoren-9-yl)methoxy]carbonyl]-L-ornithine→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→Resin bound L-prolyl-N5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-ornithylglycinamide→Resin bound Asn-Cys(Trt)-Pro-Orn(Dde)-Gly-NH→N-alpha-Fmoc-L-threonine<-fgf->N-(9H-Fluoren-9-ylmethoxycarbonyl)-L-threonine→Resin bound Thr-Asn-Cys(Trt)-Pro-Orn(Dde)-Gly→N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-asparagine→N-(9-Fluorenylmethoxycarbonyl)-L-proline→N-(9-Fluorenylmethoxycarbonyl)-S-trityl-L-cysteine→N-(9H-Fluoren-9-ylmethoxycarbonyl)glycine
Atosiban acetateOptimised routesteps: 3total yield: /
N5-[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-ornithine→1-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-L-prolyl-N5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-ornithine→Resin bound Gly-NH→N-(9-Fluorenylmethoxycarbonyl)-L-proline→Resin bound L-prolyl-N5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-ornithylglycinamide
EptifibatideOriginator routesteps: 8total yield: /
(7S,13S)-tert-butyl 13-(((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)carbamoyl)-7-(4-aminobutyl)-5,8,11-trioxo-1,1,1-triphenyl-2-thia-6,9,12-triazapentadecan-15-oate→3,5-dimethyl-1H-pyrazole-1-carboximidamide→N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine→(9H-fluoren-9-yl)methyl (R)-(1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamate→(((9H-fluoren-9-yl)methoxy)carbonyl)-L-proline→(9H-fluoren-9-yl)methyl (S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidine-1-carboxylate→Na-(((9H-fluoren-9-yl)methoxy)carbonyl)-1-(tert-butoxycarbonyl)-L-tryptophan→(9H-fluoren-9-yl)methyl ((S)-3-(1H-indol-3-yl)-1-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)carbamate→(S)-tert-butyl 4-(((S)-3-(1H-indol-3-yl)-1-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)amino)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-oxobutanoate→(((9H-fluoren-9-yl)methoxy)carbonyl)glycine→(S)-tert-butyl 4-(((S)-3-(1H-indol-3-yl)-1-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)amino)-3-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)acetamido)-4-oxobutanoate→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)hexanoic acid→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid→(10S,16S)-tert-butyl 16-(((S)-3-(1H-indol-3-yl)-1-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)carbamoyl)-10-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaoctadecan-18-oate→3-(tritylthio)propanoic acid
EptifibatideOptimised routesteps: 9total yield: /
(((9H-fluoren-9-yl)methoxy)carbonyl)-L-proline→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid→3-(tritylthio)propanoic acid→methyl glycinate hydrochloride→(S)-2-(((benzyloxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)hexanoic acid→(S)-methyl 2-(2-(((benzyloxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)hexanamido)acetate→(S)-methyl 2-(6-((tert-butoxycarbonyl)amino)-2-(3-(tritylthio)propanamido)hexanamido)acetate→(S)-tert-butyl 3-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→(10S,16S)-tert-butyl 16-(((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)carbamoyl)-2,2-dimethyl-4,11,14-trioxo-10-(3-(tritylthio)propanamido)-3-oxa-5,12,15-triazaoctadecan-18-oate→2-((3R,11S,17S,20S,25aS)-20-((1H-indol-3-yl)methyl)-11-(4-aminobutyl)-3-carbamoyl-1,9,12,15,18,21-hexaoxodocosahydro-1H-pyrrolo[2,1-g][1,2,5,8,11,14,17,20]dithiahexaazacyclotricosin-17-yl)acetic acid hydrochloride→amino(imino)methanesulfonic acid hydrate→(R)-2-amino-3-(tritylthio)propanamide→(S)-(9H-fluoren-9-yl)methyl 2-(((R)-1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidine-1-carboxylate→(((9H-fluoren-9-yl)methoxy)carbonyl)-L-tryptophan→(9H-fluoren-9-yl)methyl ((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)carbamate→(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

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