((S)-5-[2-(tert-Butoxycarbonyl-methyl-amino)-ethylcarbamoyl]-5-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-pentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: ((S)-5-[2-(tert-Butoxycarbonyl-methyl-amino)-ethylcarbamoyl]-5-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-pentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 183444-93-1
• Molecular Formula: C₅₆H₆₄N₆O₉
• Molecular Weight: 965.159

Synonyms:

Chemical Property of ((S)-5-[2-(tert-Butoxycarbonyl-methyl-amino)-ethylcarbamoyl]-5-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-pentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Chemical Property:

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Technology Process of ((S)-5-[2-(tert-Butoxycarbonyl-methyl-amino)-ethylcarbamoyl]-5-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-pentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

There total 9 articles about ((S)-5-[2-(tert-Butoxycarbonyl-methyl-amino)-ethylcarbamoyl]-5-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-pentyl)-carbamic acid 9H-fluoren-9-ylmethyl 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: 50.0%

(2-aminoethyl)methylcarbamic acid tert-butyl ester (121492-06-6) + (S)-6-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-hexanoic acid (183444-90-8) → ((S)-5-[2-(tert-Butoxycarbonyl-methyl-amino)-ethylcarbamoyl]-5-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-pentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (183444-93-1)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In tetrahydrofuran; methanol;

DOI:10.1055/s-1996-4368

Reference yield:

N-(tert-butoxycarbonyl)sarcosine (13734-36-6) → ((S)-5-[2-(tert-Butoxycarbonyl-methyl-amino)-ethylcarbamoyl]-5-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-pentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (183444-93-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / chloroformic acid ethyl ester, Et₃N, 20percent aq. NH₃ / tetrahydrofuran

2: 80 percent / NMM, trifluoroacetic anhydride / tetrahydrofuran / 3 h / Ambient temperature

3: 86 percent / H₂, NH₃-sat. EtOH / Raney-Ni / 12 h / 50 °C / 22501.8 Torr

4: 50 percent / EEDQ / tetrahydrofuran; methanol

With 4-methyl-morpholine; ammonium hydroxide; ammonia; hydrogen; chloroformic acid ethyl ester; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic anhydride; nickel; In tetrahydrofuran; methanol;

DOI:10.1055/s-1996-4368

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → ((S)-5-[2-(tert-Butoxycarbonyl-methyl-amino)-ethylcarbamoyl]-5-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-pentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (183444-93-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / NaOH / dioxane

2: 69 percent / chloroformic acid ethyl ester, Et₃N, 20percent aq. NH₃ / tetrahydrofuran

3: 80 percent / NMM, trifluoroacetic anhydride / tetrahydrofuran / 3 h / Ambient temperature

4: 86 percent / H₂, NH₃-sat. EtOH / Raney-Ni / 12 h / 50 °C / 22501.8 Torr

5: 50 percent / EEDQ / tetrahydrofuran; methanol

With 4-methyl-morpholine; ammonium hydroxide; sodium hydroxide; ammonia; hydrogen; chloroformic acid ethyl ester; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic anhydride; nickel; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1055/s-1996-4368

upstream raw materials:

(2-aminoethyl)methylcarbamic acid tert-butyl ester

(S)-6-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-hexanoic acid

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)sarcosine

Downstream raw materials:

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

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

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