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CAS 71989-14-5

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid

Codes: BATIF-008, EPTI-007

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 CitrateUnstable 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-
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
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
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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