[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

Base Information

• Chemical Name: [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
• CAS No.: 371111-53-4
• Molecular Formula: C₄₈H₆₃N₅O₉
• Molecular Weight: 854.056
• Mol file: 371111-53-4.mol

Synonyms:[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

Chemical Property of [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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [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

There total 17 articles about [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 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-hydroxy-3-nitrohexanoic acid (367258-42-2) → [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)

Guidance literature:

Multi-step reaction with 7 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

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; hydrogen; benzotriazol-1-ol; 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;

DOI:10.1021/jm0489556

Reference yield:

ethyl-5-(4-chlorophenyl)pent-2-enoate (371111-50-1) → [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)

Guidance literature:

Multi-step reaction with 5 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

With lithium hydroxide; hydrogen; benzotriazol-1-ol; 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;

DOI:10.1021/jm0489556

Reference yield:

3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid (166196-06-1) → [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)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / HOBt; N-methylmorpholine; EDCI / CH₂Cl₂; dimethylformamide / 12 h / -20 °C

2: H₂ / Pd/C / ethanol / 20 °C

3: 2.6 g / HOBt; EDCI*HCl / CH₂Cl₂ / 12 h / -20 °C

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

5: 230 mg / HOBt; Huenigs base; EDCI / dimethylformamide / 12 h / 0 °C

With 4-methyl-morpholine; hydrogenchloride; hydrogen; benzotriazol-1-ol; 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;

DOI:10.1021/jm0489556

upstream raw materials:

2-hydroxy-3-nitrohexanoic acid

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

3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid

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

Downstream raw materials:

(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