[4-({2-[5-((S)-2-Amino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-benzyloxycarbonyl-amino)-butyl]-carbamic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: [4-({2-[5-((S)-2-Amino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-benzyloxycarbonyl-amino)-butyl]-carbamic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 121903-73-9
• Molecular Formula: C₂₇H₄₁Cl₃N₆O₇
• Molecular Weight: 668.018

Synonyms:

Chemical Property of [4-({2-[5-((S)-2-Amino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-benzyloxycarbonyl-amino)-butyl]-carbamic acid 2,2,2-trichloro-ethyl ester

Chemical Property:

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Technology Process of [4-({2-[5-((S)-2-Amino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-benzyloxycarbonyl-amino)-butyl]-carbamic acid 2,2,2-trichloro-ethyl ester

There total 10 articles about [4-({2-[5-((S)-2-Amino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-benzyloxycarbonyl-amino)-butyl]-carbamic acid 2,2,2-trichloro-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:

1,5-diaminopentane (462-94-2) → [4-({2-[5-((S)-2-Amino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-benzyloxycarbonyl-amino)-butyl]-carbamic acid 2,2,2-trichloro-ethyl ester (121903-73-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 62.7 percent / triethylamine / methanol; tetrahydrofuran / 1 h

2: HOBt, C₂H₅N=C=N(CH₂)3N(CH₃)2 / dimethylformamide / Ambient temperature

3: N₂H₄ / ethanol / 2 h / Heating

4: Et₃N / ethyl acetate / 2.5 h

5: trifluoroacetic acid / 0.75 h / Ambient temperature

6: Et₃N / dimethylformamide / 36 h / Ambient temperature

7: trifluoroacetic acid / 0.83 h / Ambient temperature

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; hydrazine; In tetrahydrofuran; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1016/S0040-4020(01)86395-X

Reference yield:

N-(tert-butoxycarbonyl)-1,5-diaminopentane hydrochloride (77835-31-5) → [4-({2-[5-((S)-2-Amino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-benzyloxycarbonyl-amino)-butyl]-carbamic acid 2,2,2-trichloro-ethyl ester (121903-73-9)

Guidance literature:

Multi-step reaction with 6 steps

1: HOBt, C₂H₅N=C=N(CH₂)3N(CH₃)2 / dimethylformamide / Ambient temperature

2: N₂H₄ / ethanol / 2 h / Heating

3: Et₃N / ethyl acetate / 2.5 h

4: trifluoroacetic acid / 0.75 h / Ambient temperature

5: Et₃N / dimethylformamide / 36 h / Ambient temperature

6: trifluoroacetic acid / 0.83 h / Ambient temperature

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; hydrazine; In ethanol; ethyl acetate; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1016/S0040-4020(01)86395-X

Reference yield:

Boc->Cad<-Pua(Z)=Pht (113953-96-1) → [4-({2-[5-((S)-2-Amino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-benzyloxycarbonyl-amino)-butyl]-carbamic acid 2,2,2-trichloro-ethyl ester (121903-73-9)

Guidance literature:

Multi-step reaction with 5 steps

1: N₂H₄ / ethanol / 2 h / Heating

2: Et₃N / ethyl acetate / 2.5 h

3: trifluoroacetic acid / 0.75 h / Ambient temperature

4: Et₃N / dimethylformamide / 36 h / Ambient temperature

5: trifluoroacetic acid / 0.83 h / Ambient temperature

With triethylamine; hydrazine; In ethanol; ethyl acetate; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1016/S0040-4020(01)86395-X

upstream raw materials:

Boc->Cad<-Pua(Z)=Pht

1,5-diaminopentane

N-(tert-butoxycarbonyl)-1,5-diaminopentane hydrochloride

Boc->Cad<-Pua(Z)=Pht

Downstream raw materials:

2,4-dibenzyloxyphenylacetyl-L-Asn->Cad<-Pua(Z)-H

2,4-dibenzyloxyphenylacetyl-L-Asn->Cad<-Pua(Z)-Troc

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