N-(2-chloroethyl)-N'-{2-[D-(N-tert-butoxycarbonylalanyl)-L-phenylalanyl-L-(N^Ω-tert-butoxycarbonyl)lysylamino]ethyl}-N-nitrosourea

Base Information

• Chemical Name: N-(2-chloroethyl)-N'-{2-[D-(N-tert-butoxycarbonylalanyl)-L-phenylalanyl-L-(N^Ω-tert-butoxycarbonyl)lysylamino]ethyl}-N-nitrosourea
• CAS No.: 183444-84-0
• Molecular Formula: C₃₃H₅₃ClN₈O₉
• Molecular Weight: 741.285

Synonyms:N-(2-chloroethyl)-N'-{2-[D-(N-tert-butoxycarbonylalanyl)-L-phenylalanyl-L-(N^Ω-tert-butoxycarbonyl)lysylamino]ethyl}-N-nitrosourea

Chemical Property of N-(2-chloroethyl)-N'-{2-[D-(N-tert-butoxycarbonylalanyl)-L-phenylalanyl-L-(N^Ω-tert-butoxycarbonyl)lysylamino]ethyl}-N-nitrosourea

Chemical Property:

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Technology Process of N-(2-chloroethyl)-N'-{2-[D-(N-tert-butoxycarbonylalanyl)-L-phenylalanyl-L-(N^Ω-tert-butoxycarbonyl)lysylamino]ethyl}-N-nitrosourea

There total 6 articles about N-(2-chloroethyl)-N'-{2-[D-(N-tert-butoxycarbonylalanyl)-L-phenylalanyl-L-(N^Ω-tert-butoxycarbonyl)lysylamino]ethyl}-N-nitrosourea 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:

Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3) → N-(2-chloroethyl)-N'-{2-[D-(N-tert-butoxycarbonylalanyl)-L-phenylalanyl-L-(NΩ-tert-butoxycarbonyl)lysylamino]ethyl}-N-nitrosourea (183444-84-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 61 percent / 1-hydroxybenzotriazole, Et₃N, DCC / dimethylformamide; CH₂Cl₂ / 24 h / Ambient temperature

2: 1 M aq. NaOH / acetone; dimethylformamide / 1 h / Ambient temperature

3: NMM, , N-hydroxypyrrolidine-2,5-dione, DCC, Et₃N / dimethylformamide; CH₂Cl₂ / 24 h / Ambient temperature

4: 80 percent / NMM, EEDQ / tetrahydrofuran / Ambient temperature

5: H₂ / 10percent Pd/C / methanol

6: NMM / tetrahydrofuran / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; benzotriazol-1-ol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1055/s-1996-4368

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → N-(2-chloroethyl)-N'-{2-[D-(N-tert-butoxycarbonylalanyl)-L-phenylalanyl-L-(NΩ-tert-butoxycarbonyl)lysylamino]ethyl}-N-nitrosourea (183444-84-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 61 percent / 1-hydroxybenzotriazole, Et₃N, DCC / dimethylformamide; CH₂Cl₂ / 24 h / Ambient temperature

2: 1 M aq. NaOH / acetone; dimethylformamide / 1 h / Ambient temperature

3: NMM, , N-hydroxypyrrolidine-2,5-dione, DCC, Et₃N / dimethylformamide; CH₂Cl₂ / 24 h / Ambient temperature

4: 80 percent / NMM, EEDQ / tetrahydrofuran / Ambient temperature

5: H₂ / 10percent Pd/C / methanol

6: NMM / tetrahydrofuran / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; benzotriazol-1-ol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1055/s-1996-4368

Reference yield:

D-(N-tert-butoxycarbonylalanyl)-L-phenylalanine (94883-19-9) → N-(2-chloroethyl)-N'-{2-[D-(N-tert-butoxycarbonylalanyl)-L-phenylalanyl-L-(NΩ-tert-butoxycarbonyl)lysylamino]ethyl}-N-nitrosourea (183444-84-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NMM, , N-hydroxypyrrolidine-2,5-dione, DCC, Et₃N / dimethylformamide; CH₂Cl₂ / 24 h / Ambient temperature

2: 80 percent / NMM, EEDQ / tetrahydrofuran / Ambient temperature

3: H₂ / 10percent Pd/C / methanol

4: NMM / tetrahydrofuran / Ambient temperature

With 4-methyl-morpholine; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1996-4368

upstream raw materials:

N-(2-chloroethyl)-N-nitrosocarbamic acid N-hydroxypyrrolidine-2,5-dione ester

Boc-(R)-Ala

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

D-(N-tert-butoxycarbonylalanyl)-L-phenylalanine

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