N₄-(2,2-dimethylpropyl)-N₁-(1-{1-(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-(S)-methylbutylcarbamoyl}-2-methoxyethyl)-2(S)-(toluene-4-sulfonylamino)succinamide

Base Information

• Chemical Name: N₄-(2,2-dimethylpropyl)-N₁-(1-{1-(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-(S)-methylbutylcarbamoyl}-2-methoxyethyl)-2(S)-(toluene-4-sulfonylamino)succinamide
• CAS No.: 660847-71-2
• Molecular Formula: C₃₄H₄₈N₆O₈S
• Molecular Weight: 700.857

Synonyms:N₄-(2,2-dimethylpropyl)-N₁-(1-{1-(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-(S)-methylbutylcarbamoyl}-2-methoxyethyl)-2(S)-(toluene-4-sulfonylamino)succinamide

Chemical Property of N₄-(2,2-dimethylpropyl)-N₁-(1-{1-(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-(S)-methylbutylcarbamoyl}-2-methoxyethyl)-2(S)-(toluene-4-sulfonylamino)succinamide

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Technology Process of N₄-(2,2-dimethylpropyl)-N₁-(1-{1-(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-(S)-methylbutylcarbamoyl}-2-methoxyethyl)-2(S)-(toluene-4-sulfonylamino)succinamide

There total 9 articles about N₄-(2,2-dimethylpropyl)-N₁-(1-{1-(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-(S)-methylbutylcarbamoyl}-2-methoxyethyl)-2(S)-(toluene-4-sulfonylamino)succinamide 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: 37.0%

(S)-2-(4-methylphenylsulfonamido)-4-(neopentylamino)-4-oxobutanoic acid (890660-09-0) + 2-(S)-amino-N-{1(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-methylbutyl}-3-methoxypropionamide hydrochloride → N4-(2,2-dimethylpropyl)-N1-(1-{1-(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-(S)-methylbutylcarbamoyl}-2-methoxyethyl)-2(S)-(toluene-4-sulfonylamino)succinamide (660847-71-2)

Guidance literature:

(S)-2-(4-methylphenylsulfonamido)-4-(neopentylamino)-4-oxobutanoic acid; With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 0.133333h;

2-(S)-amino-N-{1(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-methylbutyl}-3-methoxypropionamide hydrochloride; With 4-methyl-morpholine; In dichloromethane; for 2.5h;

Reference yield:

{1-[(R/S)-hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-methylbutyl}carbamic acid tert-butyl ester (660847-45-0) → N4-(2,2-dimethylpropyl)-N1-(1-{1-(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-(S)-methylbutylcarbamoyl}-2-methoxyethyl)-2(S)-(toluene-4-sulfonylamino)succinamide (660847-71-2)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / CH₂Cl₂; dioxane / 2 h

2: 79 percent / HOBT; EDC; N-methylmorpholine / CH₂Cl₂ / 3 h

3: HCl / dioxane / 2 h

4: HOBT; EDC; N-methylmorpholine / CH₂Cl₂ / 2.5 h

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jm058289o

Reference yield:

Boc-neopentyl-Asn-O-tBu (890660-33-0) → N4-(2,2-dimethylpropyl)-N1-(1-{1-(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-(S)-methylbutylcarbamoyl}-2-methoxyethyl)-2(S)-(toluene-4-sulfonylamino)succinamide (660847-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / HCl / dioxane / 2 h

2: 60 percent / aq. NaOH / tetrahydrofuran / 2 h

3: HOBT; EDC; N-methylmorpholine / CH₂Cl₂ / 2.5 h

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 2: Schotten-Bauman reaction;

DOI:10.1021/jm058289o

upstream raw materials:

(S)-2-(4-methylphenylsulfonamido)-4-(neopentylamino)-4-oxobutanoic acid

{1-[(R/S)-hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-methylbutyl}carbamic acid tert-butyl ester

Boc-neopentyl-Asn-O-tBu

(1-{1(R/S)-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(S)-methyl]-3-methylbutylcarbamoyl}-2-(S)-methoxyethyl)carbamic acid tert-butyl ester

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