N¹-[N-(tert-butoxycarbonyl)-D-methionyl]-N²-(benzyloxycarbonyl)ethane-1,2-diamine

Base Information

• Chemical Name: N¹-[N-(tert-butoxycarbonyl)-D-methionyl]-N²-(benzyloxycarbonyl)ethane-1,2-diamine
• CAS No.: 644996-22-5
• Molecular Formula: C₂₀H₃₁N₃O₅S
• Molecular Weight: 425.549

Synonyms:N¹-[N-(tert-butoxycarbonyl)-D-methionyl]-N²-(benzyloxycarbonyl)ethane-1,2-diamine

Chemical Property of N¹-[N-(tert-butoxycarbonyl)-D-methionyl]-N²-(benzyloxycarbonyl)ethane-1,2-diamine

Chemical Property:

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Technology Process of N¹-[N-(tert-butoxycarbonyl)-D-methionyl]-N²-(benzyloxycarbonyl)ethane-1,2-diamine

There total 1 articles about N¹-[N-(tert-butoxycarbonyl)-D-methionyl]-N²-(benzyloxycarbonyl)ethane-1,2-diamine 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: 73.0%

(R)-N-(tert-butoxycarbonyl)methionine (5241-66-7) + benzyl N-(2-aminoethyl)carbamate hydrochloride (18807-71-1) → N1-[N-(tert-butoxycarbonyl)-D-methionyl]-N2-(benzyloxycarbonyl)ethane-1,2-diamine (644996-22-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at -78 - 20 ℃;

DOI:10.1016/S0968-0896(03)00396-1

Reference yield: 53.0%

N1-[N-(tert-butoxycarbonyl)-D-methionyl]-N2-(benzyloxycarbonyl)ethane-1,2-diamine (644996-22-5) → N-[2-[(benzyloxycarbonyl)amino]ethyl]-3(R)-[(tert-butoxycarbonyl)amino]pyrrolidin-2-one (644996-23-6)

Guidance literature:

N¹-[N-(tert-butoxycarbonyl)-D-methionyl]-N²-(benzyloxycarbonyl)ethane-1,2-diamine; With methyl iodide; at 20 ℃;

With sodium hydride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 51h;

DOI:10.1016/S0968-0896(03)00396-1

Reference yield:

N1-[N-(tert-butoxycarbonyl)-D-methionyl]-N2-(benzyloxycarbonyl)ethane-1,2-diamine (644996-22-5) → N-[2-[(benzyloxycarbonyl)amino]ethyl]-3(R)-[[1-(benzyloxycarbonyl)-2(S)-pyrrolidinylcarbonyl]amino]pyrrolidin-2-one (644996-24-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: MeI / 20 °C

1.2: 53 percent / NaH / CH₂Cl₂; dimethylformamide / 51 h / 0 - 20 °C

2.1: HCl / dioxane / 5 h

2.2: 32 percent / HOBt*H₂O; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et₃N / CH₂Cl₂; dimethylformamide / -78 - 20 °C

With hydrogenchloride; methyl iodide; In 1,4-dioxane;

DOI:10.1016/S0968-0896(03)00396-1

upstream raw materials:

(R)-N-(tert-butoxycarbonyl)methionine

benzyl N-(2-aminoethyl)carbamate hydrochloride

Downstream raw materials:

N-[2-[(benzyloxycarbonyl)amino]ethyl]-3(R)-[(tert-butoxycarbonyl)amino]pyrrolidin-2-one

N-[2-[(benzyloxycarbonyl)amino]ethyl]-3(R)-[[1-(benzyloxycarbonyl)-2(S)-pyrrolidinylcarbonyl]amino]pyrrolidin-2-one

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