(S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

Base Information

• Chemical Name: (S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester
• CAS No.: 371111-74-9
• Molecular Formula: C₄₅H₆₅N₅O₈
• Molecular Weight: 804.04

Synonyms:(S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

Chemical Property of (S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

There total 12 articles about (S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-hydroxy-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: 73.0%

(3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1(19),16(20),17-triene-3-carboxylic acid + ({2-[(3-amino-2-hydroxyhexanoyl)amino]acetyl}amino)(phenyl)acetic acid tert-butyl ester hydrochloride → (S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1(19),16(20),17-triene-3-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester (371111-74-9)

Guidance literature:

With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In dichloromethane; N,N-dimethyl-formamide; at -20 ℃;

DOI:10.1016/j.bmcl.2005.07.033

Reference yield:

3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid (166196-06-1) → (S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1(19),16(20),17-triene-3-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester (371111-74-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

2: 98 percent / H₂ / Pd/C / ethanol / 20 °C

3: 81 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

4: 100 percent / HCl / dioxane; ethyl acetate / 20 °C

5: 73 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

With 4-methyl-morpholine; hydrogenchloride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.07.033

Reference yield:

(3-tert-butoxycarbonylamino-2-hydroxyhexanoylamino)acetic acid benzyl ester (367258-43-3) → (S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1(19),16(20),17-triene-3-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester (371111-74-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / H₂ / Pd/C / ethanol / 20 °C

2: 81 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

3: 100 percent / HCl / dioxane; ethyl acetate / 20 °C

4: 73 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

With 4-methyl-morpholine; hydrogenchloride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.07.033

upstream raw materials:

3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid

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

(3-tert-butoxycarbonylamino-2-hydroxyhexanoylamino)acetic acid benzyl ester

(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester

Downstream raw materials:

(S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid

(S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

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