methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanamido)-3-phenylpropanoate

Base Information

• Chemical Name: methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanamido)-3-phenylpropanoate
• CAS No.: 1613312-94-9
• Molecular Formula: C₃₀H₃₇N₃O₅
• Molecular Weight: 519.641

Synonyms:methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanamido)-3-phenylpropanoate

Chemical Property of methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanamido)-3-phenylpropanoate

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Technology Process of methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanamido)-3-phenylpropanoate

There total 5 articles about methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanamido)-3-phenylpropanoate 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: 75.0%

(S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanoic acid (1613312-92-7) + methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanamido)-3-phenylpropanoate (1613312-94-9)

Guidance literature:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride; With 4-methyl-morpholine; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

(S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanoic acid; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1080/00397911.2014.882002

Reference yield:

tert-butyl (S,E)-2,2-dimethyl-4-(4-(quinolin-3-yl)but-3-enyl)oxazolidine-3-carboxylate (1613312-89-2) → methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanamido)-3-phenylpropanoate (1613312-94-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C

2.1: chromium(VI) oxide; sulfuric acid / water; acetone / 5 h / 0 °C

3.1: 4-methyl-morpholine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

3.2: 0.17 h / 0 °C / Inert atmosphere

3.3: 18 h / 0 - 20 °C / Inert atmosphere

With 4-methyl-morpholine; chromium(VI) oxide; sulfuric acid; palladium 10% on activated carbon; hydrogen; In methanol; dichloromethane; water; acetone; 2.1: |Jones Oxidation;

DOI:10.1080/00397911.2014.882002

Reference yield:

3-bromoquinoline (5332-24-1) → methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanamido)-3-phenylpropanoate (1613312-94-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium diacetate; tetrabutylammomium bromide; sodium hydrogencarbonate / N,N-dimethyl-formamide / 18 h / 90 °C / Sealed tube

2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C

3.1: chromium(VI) oxide; sulfuric acid / water; acetone / 5 h / 0 °C

4.1: 4-methyl-morpholine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

4.2: 0.17 h / 0 °C / Inert atmosphere

4.3: 18 h / 0 - 20 °C / Inert atmosphere

With 4-methyl-morpholine; chromium(VI) oxide; sulfuric acid; palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; palladium diacetate; sodium hydrogencarbonate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.1: |Heck Reaction / 3.1: |Jones Oxidation;

DOI:10.1080/00397911.2014.882002

upstream raw materials:

(S)-2-(tert-butoxycarbonylamino)-6-(quinolin-3-yl)hexanoic acid

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

tert-butyl (S,E)-2,2-dimethyl-4-(4-(quinolin-3-yl)but-3-enyl)oxazolidine-3-carboxylate

tert-butyl (S)-2,2-dimethyl-4-(4-(quinolin-3-yl)butyl)oxazolidine-3-carboxylate

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