4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (S)-2-((R)-2-benzylsulfanyl-1-ethoxycarbonyl-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl ester

Base Information

• Chemical Name: 4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (S)-2-((R)-2-benzylsulfanyl-1-ethoxycarbonyl-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl ester
• CAS No.: 182802-14-8
• Molecular Formula: C₃₄H₄₇Cl₂N₃O₇S
• Molecular Weight: 712.735

Synonyms:

Chemical Property of 4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (S)-2-((R)-2-benzylsulfanyl-1-ethoxycarbonyl-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl ester

Chemical Property:

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Technology Process of 4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (S)-2-((R)-2-benzylsulfanyl-1-ethoxycarbonyl-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl ester

There total 4 articles about 4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (S)-2-((R)-2-benzylsulfanyl-1-ethoxycarbonyl-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl 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: 71.0%

ethyl N-tert-butoxycarbonyl-L-seryl-S-benzyl-L-cysteine (182802-13-7) + chlorambucil (305-03-3) → 4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (S)-2-((R)-2-benzylsulfanyl-1-ethoxycarbonyl-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl ester (182802-14-8)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 6h;

DOI:10.1139/v96-167

Reference yield:

S-benzyl-L-cysteine (3054-01-1,25988-62-9) → 4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (S)-2-((R)-2-benzylsulfanyl-1-ethoxycarbonyl-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl ester (182802-14-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / 48 h / Heating

2: 1.) Na₂CO₃, 2.) EDAC - HCl / 1.) H₂O, CH₂Cl₂, 2.) CH₂Cl₂, 16 h

3: 71 percent / EDAC - HCl, DMAP / CH₂Cl₂ / 6 h

With dmap; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1139/v96-167

Reference yield:

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) → 4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (S)-2-((R)-2-benzylsulfanyl-1-ethoxycarbonyl-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl ester (182802-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Na₂CO₃, 2.) EDAC - HCl / 1.) H₂O, CH₂Cl₂, 2.) CH₂Cl₂, 16 h

2: 71 percent / EDAC - HCl, DMAP / CH₂Cl₂ / 6 h

With dmap; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1139/v96-167

upstream raw materials:

ethyl N-tert-butoxycarbonyl-L-seryl-S-benzyl-L-cysteine

chlorambucil

S-benzyl-L-cysteine

(S)-N-(tert-butoxycarbonyl)serine

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