(S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester

Base Information

• Chemical Name: (S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester
• CAS No.: 371111-11-4
• Molecular Formula: C₅₄H₆₄N₆O₁₁
• Molecular Weight: 973.136

Synonyms:(S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester

Chemical Property of (S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester

Chemical Property:

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Technology Process of (S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester

There total 13 articles about (S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl 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-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-9-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester (371111-93-2) → (S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester (371111-11-4)

Guidance literature:

With Dess-Martin periodane; In tetrahydrofuran; dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jm0489556

Reference yield:

2-hydroxy-3-nitrohexanoic acid (367258-42-2) → (S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester (371111-11-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 66 percent / H₂; AcOH / Pd/C / 3051.17 - 3102.89 Torr

2.1: 89 percent / aq. NaOH / dioxane / 0 - 20 °C

3.1: 94 percent / HOBt; N-methylmorpholine; EDCI / CH₂Cl₂; dimethylformamide / 12 h / -20 °C

4.1: H₂ / Pd/C / ethanol / 20 °C

5.1: HOBt; EDCI / CH₂Cl₂; dimethylformamide / 12 h / -20 °C

6.1: HCl / dioxane

7.1: HOBt; Huenigs base; EDCI / CH₂Cl₂ / 0.5 h / 0 °C

7.2: 138 mg / CH₂Cl₂ / 12 h / cooling

8.1: Dess-Martin periodinane / CH₂Cl₂; tetrahydrofuran / 2 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; 8.1: Dess-Martin oxidation;

DOI:10.1021/jm0489556

Reference yield:

3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid (166196-06-1) → (S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester (371111-11-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 94 percent / HOBt; N-methylmorpholine; EDCI / CH₂Cl₂; dimethylformamide / 12 h / -20 °C

2.1: H₂ / Pd/C / ethanol / 20 °C

3.1: HOBt; EDCI / CH₂Cl₂; dimethylformamide / 12 h / -20 °C

4.1: HCl / dioxane

5.1: HOBt; Huenigs base; EDCI / CH₂Cl₂ / 0.5 h / 0 °C

5.2: 138 mg / CH₂Cl₂ / 12 h / cooling

6.1: Dess-Martin periodinane / CH₂Cl₂; tetrahydrofuran / 2 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; 6.1: Dess-Martin oxidation;

DOI:10.1021/jm0489556

upstream raw materials:

(S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester

2-hydroxy-3-nitrohexanoic acid

3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid

({3-[(tert-butoxycarbonyl)amino]-2-hydroxyhexanoyl}amino)acetic acid

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