(S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid

Base Information

• Chemical Name: (S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid
• CAS No.: 1542166-89-1
• Molecular Formula: C₃₄H₄₁N₃O₆
• Molecular Weight: 587.716

Synonyms:(S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid

Chemical Property of (S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid

Chemical Property:

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Technology Process of (S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid

There total 1 articles about (S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid 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: 84.0%

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) + (S)-2-Amino-N-trityl-succinamic acid (132388-58-0,200192-49-0) → (S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid (1542166-89-1)

Guidance literature:

With sodium tris(acetoxy)borohydride; In dichloromethane; at 25 ℃; for 12.25h; Molecular sieve; Inert atmosphere;

DOI:10.1021/ja412298c

Reference yield: 81.0%

(S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid (1542166-89-1) → (S)-tert-butyl 4-((((S)-1-amino-1,4-dioxo-4-(tritylamino)butan-2-yl)amino)methyl)-2,2-dimethyloxazolidine-3-carboxylate (1542166-90-4)

Guidance literature:

(S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 25 ℃; for 0.5h; Inert atmosphere;

With ammonia; In tetrahydrofuran; dichloromethane; at 0 - 25 ℃; for 0.5h;

DOI:10.1021/ja412298c

Reference yield:

(S)-2-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-4-oxo-4-(tritylamino)butanoic acid (1542166-89-1) → C49H61N5O10

Guidance literature:

Multi-step reaction with 7 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 - 25 °C / Inert atmosphere

1.2: 0.5 h / 0 - 25 °C

2.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran; ethyl acetate / 2 h / 0 - 50 °C

3.1: hydroxylamine / water; ethanol / 12 h / 25 °C

4.1: acetic acid / water; methanol / 25 °C

5.1: acetonitrile / 15 h / 25 °C / Molecular sieve

6.1: triethylamine / tetrahydrofuran / 12 h / 50 °C

7.1: sodium hydroxide; water / tetrahydrofuran; methanol / 0.17 h / 0 °C

With water; hydroxylamine; benzotriazol-1-ol; acetic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetonitrile; 5.1: |Diels-Alder Cycloaddition;

DOI:10.1021/ja412298c

upstream raw materials:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(S)-2-Amino-N-trityl-succinamic acid

Downstream raw materials:

(S)-tert-butyl 4-((((S)-1-amino-1,4-dioxo-4-(tritylamino)butan-2-yl)amino)methyl)-2,2-dimethyloxazolidine-3-carboxylate

(S)-tert-butyl 4-((((S)-1-cyano-3-oxo-3-(tritylamino)propyl)amino)methyl)-2,2-dimethyloxazolidine-3-carboxylate

(S)-tert-butyl 4-((((S)-1-amino-1-(hydroxyimino)-4-oxo-4-(tritylamino)butan-2-yl)amino)methyl)-2,2-dimethyloxazolidine-3-carboxylate

4-tert-butyl 6-ethyl 2-((S)-1-((((S)-3-(tert-butyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)methyl)amino)-3-oxo-3-(tritylamino)propyl)-5-methylpyrimidine-4,6-dicarboxylate

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