N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris{N¹-[2-(tert-butoxycarbonylamino)ethyl]-L-valinamide}

Base Information

• Chemical Name: N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris{N¹-[2-(tert-butoxycarbonylamino)ethyl]-L-valinamide}
• CAS No.: 197637-16-4
• Molecular Formula: C₆₃H₉₃N₁₃O₁₅
• Molecular Weight: 1272.51

Synonyms:N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris{N¹-[2-(tert-butoxycarbonylamino)ethyl]-L-valinamide}

Chemical Property of N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris{N¹-[2-(tert-butoxycarbonylamino)ethyl]-L-valinamide}

Chemical Property:

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Technology Process of N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris{N¹-[2-(tert-butoxycarbonylamino)ethyl]-L-valinamide}

There total 6 articles about N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris{N¹-[2-(tert-butoxycarbonylamino)ethyl]-L-valinamide} 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: 85.0%

N-BOC-1,2-diaminoethane (57260-73-8) + N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris(L-valine) (197636-81-0) → N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris{N1-[2-(tert-butoxycarbonylamino)ethyl]-L-valinamide} (197637-16-4)

Guidance literature:

With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; 1.) 0 deg C, 1 h, 2.) 0 deg C to r.t., 23 h;

DOI:10.1002/chem.19970030813

Reference yield:

L-valine methylester hydrochloride (6306-52-1) → N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris{N1-[2-(tert-butoxycarbonylamino)ethyl]-L-valinamide} (197637-16-4)

Guidance literature:

Multi-step reaction with 3 steps

1: HOBt, N-ethylmorpholine, EDCl / tetrahydrofuran / 18 h / 0 - 20 °C

2: 93 percent / aq. LiOH / tetrahydrofuran / 1.) 0 deg C, 3 h, 2.) r.t., 15 h

3: 85 percent / HOBt, N-ethylmorpholine, EDCl / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 0 deg C to r.t., 23 h

With N-ethylmorpholine;; lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran;

DOI:10.1002/chem.19970030813

Reference yield:

(RRS/SSR)-Trimethyl 2,2',2''-nitrilotris<2-(benzoylamino)acetate> → N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris{N1-[2-(tert-butoxycarbonylamino)ethyl]-L-valinamide} (197637-16-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaOMe, 2.) aq. LiOH / 1.) MeOH, THF, r.t., 24 h, 2.) MeOH, r.t., 24 h

2: HOBt, N-ethylmorpholine, EDCl / tetrahydrofuran / 18 h / 0 - 20 °C

3: 93 percent / aq. LiOH / tetrahydrofuran / 1.) 0 deg C, 3 h, 2.) r.t., 15 h

4: 85 percent / HOBt, N-ethylmorpholine, EDCl / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 0 deg C to r.t., 23 h

With N-ethylmorpholine;; lithium hydroxide; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran;

DOI:10.1002/chem.19970030813

upstream raw materials:

N-BOC-1,2-diaminoethane

N,N',N''-{(SSS)-Nitrilotris[2-(benzoylamino)-1-oxo-2,1-ethanediyl]}tris(L-valine)

L-valine methylester hydrochloride

N,N',N''-<(SSS)-Nitrilotris<2-(benzoylamino)-1-oxo-2,1-ethanediyl>>tris trimethyl ester

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