N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(N^ω-9-fluorenylmethoxycarbonyllysyl)amino]ethyl}-N-nitrosourea

Base Information

• Chemical Name: N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(N^ω-9-fluorenylmethoxycarbonyllysyl)amino]ethyl}-N-nitrosourea
• CAS No.: 183444-97-5
• Molecular Formula: C₅₄H₅₉ClN₈O₉
• Molecular Weight: 999.564

Synonyms:N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(N^ω-9-fluorenylmethoxycarbonyllysyl)amino]ethyl}-N-nitrosourea

Chemical Property of N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(N^ω-9-fluorenylmethoxycarbonyllysyl)amino]ethyl}-N-nitrosourea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(N^ω-9-fluorenylmethoxycarbonyllysyl)amino]ethyl}-N-nitrosourea

There total 7 articles about N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(N^ω-9-fluorenylmethoxycarbonyllysyl)amino]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: 92.0%

N-(2-chloroethyl)-N-nitrosocarbamic acid N-hydroxypyrrolidine-2,5-dione ester (80354-49-0) + [(S)-5-{(S)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-5-(2-methylamino-ethylcarbamoyl)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester; hydrochloride → N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(Nω-9-fluorenylmethoxycarbonyllysyl)amino]ethyl}-N-nitrosourea (183444-97-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; at 0 ℃; for 2.5h;

DOI:10.1055/s-1996-4368

Reference yield:

L-phenylalanine tert-butyl ester (16874-17-2) → N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(Nω-9-fluorenylmethoxycarbonyllysyl)amino]ethyl}-N-nitrosourea (183444-97-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) N-hydroxypyrrolidine-2,5-dione, DCC / 1.) THF, 0 deg C, 2 h, 2.) THF, RT, overnight

2: 87 percent / 2 M aq. HBr / acetic acid

3: 1.) N-hydroxypyrrolidine-2,5-dione, DCC, 2.) NMM / 1.) THF, CH₂Cl₂, a) 0 deg C, 2 h, b) RT, overnight, 2.) THF, CH₂Cl₂, H₂O, a) 0 deg C, 2 h, b) from 0 deg C to RT, 12 h

4: 50 percent / EEDQ / tetrahydrofuran; methanol

5: 74 percent / 2 M methanolic HCl / 40 h

6: 92 percent / Huenig's base / tetrahydrofuran; methanol / 2.5 h / 0 °C

With 4-methyl-morpholine; hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen bromide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; acetic acid;

DOI:10.1055/s-1996-4368

Reference yield:

N-(9-fluorenylmethoxycarbonyl)-D-alanine (35661-38-2,35661-39-3,79990-15-1,136132-75-7) → N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(Nω-9-fluorenylmethoxycarbonyllysyl)amino]ethyl}-N-nitrosourea (183444-97-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) N-hydroxypyrrolidine-2,5-dione, DCC / 1.) THF, 0 deg C, 2 h, 2.) THF, RT, overnight

2: 87 percent / 2 M aq. HBr / acetic acid

3: 1.) N-hydroxypyrrolidine-2,5-dione, DCC, 2.) NMM / 1.) THF, CH₂Cl₂, a) 0 deg C, 2 h, b) RT, overnight, 2.) THF, CH₂Cl₂, H₂O, a) 0 deg C, 2 h, b) from 0 deg C to RT, 12 h

4: 50 percent / EEDQ / tetrahydrofuran; methanol

5: 74 percent / 2 M methanolic HCl / 40 h

6: 92 percent / Huenig's base / tetrahydrofuran; methanol / 2.5 h / 0 °C

With 4-methyl-morpholine; hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen bromide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; acetic acid;

DOI:10.1055/s-1996-4368

upstream raw materials:

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

L-phenylalanine tert-butyl ester

N-(9-fluorenylmethoxycarbonyl)-D-alanine

D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanine

Downstream raw materials:

N-(2-chloroethyl)-N'-methyl-N'-[2-(D-alanyl-L-phenylalanyl-L-lysyl-amino)ethyl]-N-nitrosourea

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