(2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-yl)-4-phenyl-butyramide

Base Information

• Chemical Name: (2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-yl)-4-phenyl-butyramide
• CAS No.: 454423-73-5
• Molecular Formula: C₅₉H₆₈N₈O₈
• Molecular Weight: 1017.24

Synonyms:(2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-yl)-4-phenyl-butyramide

Chemical Property of (2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-yl)-4-phenyl-butyramide

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Technology Process of (2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-yl)-4-phenyl-butyramide

There total 5 articles about (2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-yl)-4-phenyl-butyramide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

Ac-His(1-Trt)-OH (183498-47-7) + (S)-2-Amino-N-[(1S,2R)-1-benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-ylcarbamoyl)-ethyl]-3-methyl-butyramide; hydrochloride → (2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-yl)-4-phenyl-butyramide (454423-73-5)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1016/S0968-0896(03)00054-3

Reference yield:

(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester (116565-10-7) → (2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-yl)-4-phenyl-butyramide (454423-73-5)

Guidance literature:

Multi-step reaction with 6 steps

1: LiOH / methanol; tetrahydrofuran; H₂O

2: 64 percent / HBTU; DIPEA / tetrahydrofuran / 2 h / 20 °C

3: HCl / dioxane / 20 °C

4: 58 percent / HBTU; DIPEA / dimethylformamide / 18 h / 20 °C

5: HCl / dioxane / 20 °C

6: 73 percent / HBTU; DIPEA / dimethylformamide / 4 h / 20 °C

With hydrogenchloride; lithium hydroxide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00054-3

Reference yield:

{(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester (573968-50-0) → (2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-yl)-4-phenyl-butyramide (454423-73-5)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / dioxane / 20 °C

2: 73 percent / HBTU; DIPEA / dimethylformamide / 4 h / 20 °C

With hydrogenchloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00054-3

upstream raw materials:

Ac-His(1-Trt)-OH

(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

{(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester

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