(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

Base Information

• Chemical Name: (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
• CAS No.: 144333-42-6
• Molecular Formula: C₃₁H₃₃N₃O₈
• Molecular Weight: 575.618

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (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

There total 15 articles about (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 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:

2-bromo-p-toluidine (583-68-6) → (9S,12S,15S)-15-Acetylamino-4-hydroxy-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 (144333-42-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) conc. H₂SO₄, NaNO₂, 2.) NaNO₂, NaHCO₃

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

3: 61 percent / NaH, CuBr*Me₂S / nitrobenzene / 7 h / 110 °C

4: 75 percent / t-BuOK / CH₂Cl₂ / 2 h / -60 °C

5: 98 percent / H₂ / 10percent Pd-C / methanol / 10 h / 25 °C

6: 86 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / 0 °C

7: 88 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 10 h / 0 °C

8: 1.) 1-hydroxybenzotriazole (HOBT), 1,3-dicyclohexylcarbodiimide (DCC) / 1.) CH₂Cl₂, 0 deg C, 2.) 25 deg C, 1 h

9: 90 percent / n-Bu₄NF / tetrahydrofuran; dimethylformamide / 2 h / 25 °C

10: 80 percent / 1,3-dicyclohexylcarbodiimid (DCC) / CH₂Cl₂ / 1 h / 25 °C

11: thioanisole / CH₂Cl₂ / 1 h / 0 °C

12: pyridine / dioxane / 3 h / 90 °C

13: 94 percent / H₂ / 10percent Pd-C / methanol / 2 h / 25 °C

14: 1.) 50percent HBF₄, isoamylnitrite, 2.) Cu(NO₃)2-trihydrate, CuO, H₂O / 1.) MeOH, 0 deg C, 0.5 h, 2.) 0.5 h

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; tetrafluoroboric acid; copper(I) bromide dimethylsulfide complex; methyl-phenyl-thioether; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; acetic anhydride; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; copper(II) nitrate; dicyclohexyl-carbodiimide; copper(II) oxide; sodium nitrite; isopentyl nitrite; 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-nitrotoluene (40385-54-4) → (9S,12S,15S)-15-Acetylamino-4-hydroxy-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 (144333-42-6)

Guidance literature:

Multi-step reaction with 13 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

12: 94 percent / H₂ / 10percent Pd-C / methanol / 2 h / 25 °C

13: 1.) 50percent HBF₄, isoamylnitrite, 2.) Cu(NO₃)2-trihydrate, CuO, H₂O / 1.) MeOH, 0 deg C, 0.5 h, 2.) 0.5 h

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; tetrafluoroboric acid; copper(I) bromide dimethylsulfide complex; methyl-phenyl-thioether; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; acetic anhydride; sodium hydride; benzotriazol-1-ol; copper(II) nitrate; dicyclohexyl-carbodiimide; copper(II) oxide; isopentyl nitrite; 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:

p-toluidine (106-49-0,12221-03-3) → (9S,12S,15S)-15-Acetylamino-4-hydroxy-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 (144333-42-6)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) Ac₂O, HOAc, 2.) Br₂ / 1.) reflux, 2 h, 2.) 45 deg C, 1 h

2: 1.) conc. H₂SO₄, NaNO₂, 2.) NaNO₂, NaHCO₃

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

4: 61 percent / NaH, CuBr*Me₂S / nitrobenzene / 7 h / 110 °C

5: 75 percent / t-BuOK / CH₂Cl₂ / 2 h / -60 °C

6: 98 percent / H₂ / 10percent Pd-C / methanol / 10 h / 25 °C

7: 86 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / 0 °C

8: 88 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 10 h / 0 °C

9: 1.) 1-hydroxybenzotriazole (HOBT), 1,3-dicyclohexylcarbodiimide (DCC) / 1.) CH₂Cl₂, 0 deg C, 2.) 25 deg C, 1 h

10: 90 percent / n-Bu₄NF / tetrahydrofuran; dimethylformamide / 2 h / 25 °C

11: 80 percent / 1,3-dicyclohexylcarbodiimid (DCC) / CH₂Cl₂ / 1 h / 25 °C

12: thioanisole / CH₂Cl₂ / 1 h / 0 °C

13: pyridine / dioxane / 3 h / 90 °C

14: 94 percent / H₂ / 10percent Pd-C / methanol / 2 h / 25 °C

15: 1.) 50percent HBF₄, isoamylnitrite, 2.) Cu(NO₃)2-trihydrate, CuO, H₂O / 1.) MeOH, 0 deg C, 0.5 h, 2.) 0.5 h

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; tetrafluoroboric acid; copper(I) bromide dimethylsulfide complex; methyl-phenyl-thioether; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; bromine; acetic anhydride; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; copper(II) nitrate; acetic acid; dicyclohexyl-carbodiimide; copper(II) oxide; sodium nitrite; isopentyl nitrite; 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

upstream raw materials:

(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

2-bromo-p-toluidine

3-bromo-4-nitrotoluene

p-toluidine

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