(9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid ethyl ester

Base Information

• Chemical Name: (9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid ethyl ester
• CAS No.: 144333-41-5
• Molecular Formula: C₃₉H₄₀N₄O₉
• Molecular Weight: 708.768
• Mol file: 144333-41-5.mol

Synonyms:(9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid ethyl ester

Chemical Property of (9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid ethyl ester

There total 11 articles about (9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid ethyl ester 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)-2-((S)-2-Acetylamino-3-{4-[5-((S)-2-amino-2-ethoxycarbonyl-ethyl)-2-benzyloxycarbonylamino-phenoxy]-phenyl}-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid pentafluorophenyl ester; compound with trifluoro-acetic acid → (9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid ethyl ester (144333-41-5)

Guidance literature:

With pyridine; In 1,4-dioxane; at 90 ℃; for 3h; Yield given;

DOI:10.1016/S0040-4039(00)61289-3

Reference yield:

3-bromo-4-nitrotoluene (40385-54-4) → (9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid ethyl ester (144333-41-5)

Guidance literature:

Multi-step reaction with 11 steps

1: CrO₃, conc. H₂SO₄, Ac₂O / ethanol; H₂O / 1 h / Heating

2: 61 percent / NaH, CuBr*Me₂S / nitrobenzene / 7 h / 110 °C

3: 75 percent / t-BuOK / CH₂Cl₂ / 2 h / -60 °C

4: 98 percent / H₂ / 10percent Pd-C / methanol / 10 h / 25 °C

5: 86 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / 0 °C

6: 88 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 10 h / 0 °C

7: 1.) 1-hydroxybenzotriazole (HOBT), 1,3-dicyclohexylcarbodiimide (DCC) / 1.) CH₂Cl₂, 0 deg C, 2.) 25 deg C, 1 h

8: 90 percent / n-Bu₄NF / tetrahydrofuran; dimethylformamide / 2 h / 25 °C

9: 80 percent / 1,3-dicyclohexylcarbodiimid (DCC) / CH₂Cl₂ / 1 h / 25 °C

10: thioanisole / CH₂Cl₂ / 1 h / 0 °C

11: pyridine / dioxane / 3 h / 90 °C

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; copper(I) bromide dimethylsulfide complex; methyl-phenyl-thioether; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; nitrobenzene; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)61289-3

Reference yield:

3-bromo-4-nitrobenzaldehyde (101682-68-2) → (9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid ethyl ester (144333-41-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 61 percent / NaH, CuBr*Me₂S / nitrobenzene / 7 h / 110 °C

2: 75 percent / t-BuOK / CH₂Cl₂ / 2 h / -60 °C

3: 98 percent / H₂ / 10percent Pd-C / methanol / 10 h / 25 °C

4: 86 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / 0 °C

5: 88 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 10 h / 0 °C

6: 1.) 1-hydroxybenzotriazole (HOBT), 1,3-dicyclohexylcarbodiimide (DCC) / 1.) CH₂Cl₂, 0 deg C, 2.) 25 deg C, 1 h

7: 90 percent / n-Bu₄NF / tetrahydrofuran; dimethylformamide / 2 h / 25 °C

8: 80 percent / 1,3-dicyclohexylcarbodiimid (DCC) / CH₂Cl₂ / 1 h / 25 °C

9: thioanisole / CH₂Cl₂ / 1 h / 0 °C

10: pyridine / dioxane / 3 h / 90 °C

With pyridine; dmap; lithium hydroxide; copper(I) bromide dimethylsulfide complex; methyl-phenyl-thioether; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; nitrobenzene; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)61289-3

upstream raw materials:

3-bromo-4-nitrotoluene

3-bromo-4-nitrobenzaldehyde

(S)-2-Acetylamino-3-[4-(5-formyl-2-nitro-phenoxy)-phenyl]-propionic acid methyl ester

3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-amino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester

Downstream raw materials:

(9S,12S,15S)-15-Acetylamino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid ethyl ester

(9S,12S,15S)-15-Acetylamino-4-amino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid ethyl ester