(S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3,5,7⁽²⁴⁾,19⁽²³⁾,20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

Base Information

• Chemical Name: (S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3,5,7⁽²⁴⁾,19⁽²³⁾,20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester
• CAS No.: 371110-93-9
• Molecular Formula: C₄₈H₆₁N₅O₉
• Molecular Weight: 852.04
• Mol file: 371110-93-9.mol

Synonyms:(S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3,5,7⁽²⁴⁾,19⁽²³⁾,20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

Chemical Property of (S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3,5,7⁽²⁴⁾,19⁽²³⁾,20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3,5,7⁽²⁴⁾,19⁽²³⁾,20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

There total 19 articles about (S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3,5,7⁽²⁴⁾,19⁽²³⁾,20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl 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:

[12S,9S]-(2-{3-[(12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[17.2.2.13,7]tetracosa-1(22),3(24),4,6,19(23),20-hexaene-9-carbonyl)amino]-2-hydroxyhexanoylamino}acetylamino)-[S]-phenylacetic acid tert-butyl ester (371111-53-4) → (S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.13,7]tetracosa-1(22),3,5,7(24),19(23),20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester (371110-93-9)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃;

DOI:10.1021/jm0489556

Reference yield:

2-hydroxy-3-nitrohexanoic acid (367258-42-2) → (S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.13,7]tetracosa-1(22),3,5,7(24),19(23),20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester (371110-93-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 66 percent / H₂; AcOH / Pd/C / 3051.17 - 3102.89 Torr

2: 89 percent / aq. NaOH / dioxane / 0 - 20 °C

3: 94 percent / HOBt; N-methylmorpholine; EDCI / CH₂Cl₂; dimethylformamide / 12 h / -20 °C

4: H₂ / Pd/C / ethanol / 20 °C

5: 2.6 g / HOBt; EDCI*HCl / CH₂Cl₂ / 12 h / -20 °C

6: HCl / dioxane; ethyl acetate / 0.25 h / 20 °C

7: 230 mg / HOBt; Huenigs base; EDCI / dimethylformamide / 12 h / 0 °C

8: 23 mg / Dess-Martin periodinane / CH₂Cl₂ / 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 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 8: Dess-Martin oxidation;

DOI:10.1021/jm0489556

Reference yield:

ethyl-5-(4-chlorophenyl)pent-2-enoate (371111-50-1) → (S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.13,7]tetracosa-1(22),3,5,7(24),19(23),20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester (371110-93-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / H₂ / Pd/C / ethyl acetate / 12 h / 2585.74 Torr

2: 96 percent / aq. LiOH / methanol; tetrahydrofuran / 5 h / 20 °C

3: aq. LiOH / methanol; CH₂Cl₂ / 12 h / 20 °C

4: 230 mg / HOBt; Huenigs base; EDCI / dimethylformamide / 12 h / 0 °C

5: 23 mg / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With lithium hydroxide; 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; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 6: Dess-Martin oxidation;

DOI:10.1021/jm0489556

upstream raw materials:

[12S,9S]-(2-{3-[(12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3⁽²⁴⁾,4,6,19⁽²³⁾,20-hexaene-9-carbonyl)amino]-2-hydroxyhexanoylamino}acetylamino)-[S]-phenylacetic acid tert-butyl ester

2-hydroxy-3-nitrohexanoic acid

ethyl-5-(4-chlorophenyl)pent-2-enoate

3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid