(S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester

Base Information

• Chemical Name: (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester
• CAS No.: 136015-52-6
• Molecular Formula: C₄₄H₅₃N₅O₈
• Molecular Weight: 779.934
• Mol file: 136015-52-6.mol

Synonyms:

Chemical Property of (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester

There total 8 articles about (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl 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:

di-tert-butyl dicarbonate (24424-99-5) → (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester (136015-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 0.5 N aq. NaOH / dioxane / pH 10

2: benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), NMM / dimethylformamide / 1 h / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(91)90056-S

Reference yield:

diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate (5440-57-3) → (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester (136015-52-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / 1 M NaOH / aq. ethanol / 6 h / Ambient temperature

2: 94 percent / 0.17 h / 160 °C

3: 97 percent

4: 53 percent / 6 N aq. HCl / 2 h / Heating

5: 100 percent / 0.5 N aq. NaOH / dioxane / pH 10

6: benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), NMM / dimethylformamide / 1 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(91)90056-S

Reference yield:

(S)-2-Acetylamino-3-naphthalen-1-yl-propionic acid (51684-92-5,5440-48-2) → (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester (136015-52-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 53 percent / 6 N aq. HCl / 2 h / Heating

2: 100 percent / 0.5 N aq. NaOH / dioxane / pH 10

3: benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), NMM / dimethylformamide / 1 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(91)90056-S

upstream raw materials:

(S)-2-tert-butoxycarbonylamino-3-naphthalen-1-yl-propionic acid

Nle-Asp(OBzl)-Phe-NH₂ TFA salt

di-tert-butyl dicarbonate

diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate

Downstream raw materials:

(S)-3-{(S)-2-[(S)-2-(2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-naphthalen-1-yl-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid

(S)-3-{(S)-2-[(S)-2-(2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-sulfooxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-naphthalen-1-yl-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid