(10S,13R)-13-((1R,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-10-isopropyl-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9,12-dione

Base Information

• Chemical Name: (10S,13R)-13-((1R,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-10-isopropyl-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9,12-dione
• CAS No.: 180968-19-8
• Molecular Formula: C₂₇H₃₈N₄O₅
• Molecular Weight: 498.623

Synonyms:(10S,13R)-13-((1R,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-10-isopropyl-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9,12-dione

Chemical Property of (10S,13R)-13-((1R,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-10-isopropyl-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9,12-dione

Chemical Property:

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Technology Process of (10S,13R)-13-((1R,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-10-isopropyl-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9,12-dione

There total 6 articles about (10S,13R)-13-((1R,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-10-isopropyl-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9,12-dione 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:

[(S)-1-(2-{2-[4-(Hydroxyimino-methyl)-phenoxy]-ethoxy}-ethylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester → (10S,13R)-13-((1R,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-10-isopropyl-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1(19),16(20),17-triene-9,12-dione (180968-19-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 44 percent / formic acid, H₂ / 10percent Pd/C / methanol / 3 h / 760 Torr

2: 51 percent / ethanol / 24 h / 80 °C

3: 0.4 M aq. LiOH / dioxane / 16 h / Ambient temperature

4: 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, dicyclohexylcarbodiimide / tetrahydrofuran / 120 h / Ambient temperature

5: 18percent aq. HCl / dioxane

With hydrogenchloride; lithium hydroxide; formic acid; hydrogen; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol;

DOI:10.1021/jm950641i

Reference yield:

[(1S,2R)-1-Benzyl-2-hydroxy-2-((10S,13R)-10-isopropyl-9,12-dioxo-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1(19),16(20),17-trien-13-yl)-ethyl]-carbamic acid tert-butyl ester (180968-15-4) → (10S,13R)-13-((1R,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-10-isopropyl-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1(19),16(20),17-triene-9,12-dione (180968-19-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1021/jm950641i

Reference yield:

(S)-2-Amino-N-{2-[2-(4-aminomethyl-phenoxy)-ethoxy]-ethyl}-3-methyl-butyramide (180968-08-5) → (10S,13R)-13-((1R,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-10-isopropyl-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1(19),16(20),17-triene-9,12-dione (180968-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 51 percent / ethanol / 24 h / 80 °C

2: 0.4 M aq. LiOH / dioxane / 16 h / Ambient temperature

3: 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, dicyclohexylcarbodiimide / tetrahydrofuran / 120 h / Ambient temperature

4: 18percent aq. HCl / dioxane

With hydrogenchloride; lithium hydroxide; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; ethanol;

DOI:10.1021/jm950641i

upstream raw materials:

[(1S,2R)-1-Benzyl-2-hydroxy-2-((10S,13R)-10-isopropyl-9,12-dioxo-2,5-dioxa-8,11,14-triaza-bicyclo[14.2.2]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-trien-13-yl)-ethyl]-carbamic acid tert-butyl ester

(S)-2-Amino-N-{2-[2-(4-aminomethyl-phenoxy)-ethoxy]-ethyl}-3-methyl-butyramide

(2R,3R,4S)-2-(4-{2-[2-((S)-2-Amino-3-methyl-butyrylamino)-ethoxy]-ethoxy}-benzylamino)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenyl-pentanoic acid

(2R,3R,4S)-2-(4-{2-[2-((S)-2-Amino-3-methyl-butyrylamino)-ethoxy]-ethoxy}-benzylamino)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

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