(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl ester

Base Information

• Chemical Name: (S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl ester
• CAS No.: 56439-61-3
• Molecular Formula: C₁₉H₂₇N₃O₆
• Molecular Weight: 393.44

Synonyms:(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl ester

Chemical Property of (S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl ester

Chemical Property:

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Technology Process of (S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl ester

There total 4 articles about (S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl 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)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl ester (56439-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / NaHCO₃ / H₂O; dioxane; dimethylformamide / 24 h / 20 °C

2: 68 percent / 1-hydroxybenzotriazole; ethyldiisopropylamine; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 24 h / 20 °C

With sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.06.005

Reference yield:

N-tert-butyloxycarbonylasparagine (7536-55-2) → (S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl ester (56439-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine (TEA) / CHCl₃ / 0.17 h / -20 °C

2: triethylamine (TEA) / CHCl₃ / 20 h / Ambient temperature

With triethylamine; In chloroform;

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) + C14H24N2O6 → (S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl ester (56439-61-3)

Guidance literature:

With triethylamine; In chloroform; for 20h; Yield given; Ambient temperature;

upstream raw materials:

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

di-tert-butyl dicarbonate

N-tert-butyloxycarbonylasparagine

Downstream raw materials:

L-asparginyl-L-phenylalanyl methyl ester

N^α-t-butyloxycarbonyl-L-valyl-L-asparginyl-L-phenylalanyl methyl ester

N^α-t-butyloxycarbonyl-L-valyl-L-asparginyl-L-phenylalanyl hydrazide

L-valyl-L-asparginyl-L-phenylalanyl-L-seryl-L-prolyl-L-asparginyl-L-tryptophane amide

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