(S)-3-[3-(4-{(S)-2-Acetylamino-2-[(S)-2-(4-hydroxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-ethyl}-phenoxy)-4-benzyloxycarbonylamino-phenyl]-2-tert-butoxycarbonylamino-propionic acid ethyl ester

Base Information

• Chemical Name: (S)-3-[3-(4-{(S)-2-Acetylamino-2-[(S)-2-(4-hydroxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-ethyl}-phenoxy)-4-benzyloxycarbonylamino-phenyl]-2-tert-butoxycarbonylamino-propionic acid ethyl ester
• CAS No.: 144333-39-1
• Molecular Formula: C₄₉H₆₂N₄O₁₂Si
• Molecular Weight: 927.136

Synonyms:(S)-3-[3-(4-{(S)-2-Acetylamino-2-[(S)-2-(4-hydroxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-ethyl}-phenoxy)-4-benzyloxycarbonylamino-phenyl]-2-tert-butoxycarbonylamino-propionic acid ethyl ester

Chemical Property of (S)-3-[3-(4-{(S)-2-Acetylamino-2-[(S)-2-(4-hydroxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-ethyl}-phenoxy)-4-benzyloxycarbonylamino-phenyl]-2-tert-butoxycarbonylamino-propionic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (S)-3-[3-(4-{(S)-2-Acetylamino-2-[(S)-2-(4-hydroxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-ethyl}-phenoxy)-4-benzyloxycarbonylamino-phenyl]-2-tert-butoxycarbonylamino-propionic acid ethyl ester

There total 17 articles about (S)-3-[3-(4-{(S)-2-Acetylamino-2-[(S)-2-(4-hydroxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-ethyl}-phenoxy)-4-benzyloxycarbonylamino-phenyl]-2-tert-butoxycarbonylamino-propionic 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) → (S)-3-[3-(4-{(S)-2-Acetylamino-2-[(S)-2-(4-hydroxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-ethyl}-phenoxy)-4-benzyloxycarbonylamino-phenyl]-2-tert-butoxycarbonylamino-propionic acid ethyl ester (144333-39-1)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; copper(I) bromide dimethylsulfide complex; sulfuric acid; potassium tert-butylate; hydrogen; acetic anhydride; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; nitrobenzene;

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

Reference yield:

3-bromo-4-nitrotoluene (40385-54-4) → (R)-3-[3-(4-{(S)-2-Acetylamino-2-[(S)-2-(4-hydroxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-ethyl}-phenoxy)-4-benzyloxycarbonylamino-phenyl]-2-tert-butoxycarbonylamino-propionic acid ethyl ester (144333-39-1)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; copper(I) bromide dimethylsulfide complex; sulfuric acid; potassium tert-butylate; hydrogen; acetic anhydride; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; nitrobenzene;

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

Reference yield:

3-bromo-4-nitrotoluene (40385-54-4) → (S)-3-[3-(4-{(S)-2-Acetylamino-2-[(S)-2-(4-hydroxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-ethyl}-phenoxy)-4-benzyloxycarbonylamino-phenyl]-2-tert-butoxycarbonylamino-propionic acid ethyl ester (144333-39-1)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; copper(I) bromide dimethylsulfide complex; sulfuric acid; potassium tert-butylate; hydrogen; acetic anhydride; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; nitrobenzene;

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

upstream raw materials:

<2-(trimethylsilyl)ethyl>-L-tyrosine

(S)-2-Acetylamino-3-{4-[2-benzyloxycarbonylamino-5-(2-tert-butoxycarbonylamino-2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-propionic acid

3-bromo-4-nitrotoluene

p-toluidine

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

(S)-2-((S)-2-Acetylamino-3-{4-[2-benzyloxycarbonylamino-5-((S)-2-tert-butoxycarbonylamino-2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid pentafluorophenyl ester

(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

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