N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide

Base Information

• Chemical Name: N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide
• CAS No.: 251309-08-7
• Molecular Formula: C₅₂H₆₁N₇O₇S₂
• Molecular Weight: 960.231

Synonyms:N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide

Chemical Property of N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide

Chemical Property:

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• Pictogram(s):  
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Useful:

Technology Process of N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide

There total 8 articles about N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide 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: 55.0%

[(S)-2-Naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetic acid (251308-92-6) + 2,2,5,7,8-Pentamethyl-chroman-6-sulfonic acid {[(S)-3-((S)-2-amino-3-oxo-3-thiazol-2-yl-propyl)-piperidin-1-yl]-imino-methyl}-amide; hydrochloride → N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide (251309-08-7)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00418-7

Reference yield:

N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine (56583-58-5,76985-10-9,58438-04-3) → N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide (251309-08-7)

Guidance literature:

Multi-step reaction with 6 steps

1: DIPCDI; HOAt; DIEA / dimethylformamide

2: 100 percent / TFA / CH₂Cl₂

3: 70 percent / Et₃N / methanol / Heating

4: 85 percent / NaH / dimethylformamide

5: 100 percent / TFA / CH₂Cl₂

6: 55 percent / HATU; HOAt; DIEA / dimethylformamide

With 1-hydroxy-7-aza-benzotriazole; 1,3-di-tert-butylcarbodiimide; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: deprotection / 3: Cyclization / 4: Alkylation / 5: Hydrolysis / 6: Condensation;

DOI:10.1016/S0960-894X(99)00418-7

Reference yield:

3-Phenylpropan-1-amine (2038-57-5) → N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide (251309-08-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 48 percent / Et₃N / methanol

2: DIPCDI; HOAt; DIEA / dimethylformamide

3: 100 percent / TFA / CH₂Cl₂

4: 70 percent / Et₃N / methanol / Heating

5: 85 percent / NaH / dimethylformamide

6: 100 percent / TFA / CH₂Cl₂

7: 55 percent / HATU; HOAt; DIEA / dimethylformamide

With 1-hydroxy-7-aza-benzotriazole; 1,3-di-tert-butylcarbodiimide; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Condensation / 3: deprotection / 4: Cyclization / 5: Alkylation / 6: Hydrolysis / 7: Condensation;

DOI:10.1016/S0960-894X(99)00418-7

upstream raw materials:

[(S)-2-Naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetic acid

3-Phenylpropan-1-amine

N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine

methyl 2-((3-phenylpropyl)amino)acetate

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