N^α-9-fluorenylmethoxycarbonyl-L-methionyl-L-threonyl-L-methionyl-L-valyl-L-leucyl-L-seryl-L-phenylalanine (2R)-methylpyrrolidinyl amide

Base Information

• Chemical Name: N^α-9-fluorenylmethoxycarbonyl-L-methionyl-L-threonyl-L-methionyl-L-valyl-L-leucyl-L-seryl-L-phenylalanine (2R)-methylpyrrolidinyl amide
• CAS No.: 220052-64-2
• Molecular Formula: C₅₇H₈₀N₈O₁₁S₂
• Molecular Weight: 1117.44

Synonyms:

Chemical Property of N^α-9-fluorenylmethoxycarbonyl-L-methionyl-L-threonyl-L-methionyl-L-valyl-L-leucyl-L-seryl-L-phenylalanine (2R)-methylpyrrolidinyl amide

Chemical Property:

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Technology Process of N^α-9-fluorenylmethoxycarbonyl-L-methionyl-L-threonyl-L-methionyl-L-valyl-L-leucyl-L-seryl-L-phenylalanine (2R)-methylpyrrolidinyl amide

There total 6 articles about N^α-9-fluorenylmethoxycarbonyl-L-methionyl-L-threonyl-L-methionyl-L-valyl-L-leucyl-L-seryl-L-phenylalanine (2R)-methylpyrrolidinyl amide 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: 53.0%

(S)-2-Amino-1-((R)-2-methyl-pyrrolidin-1-yl)-3-phenyl-propan-1-one + Nα-9-fluorenylmethoxycarbonyl-L-methionyl-L-threonyl-L-methionyl-L-valyl-L-leucyl-L-serine → Nα-9-fluorenylmethoxycarbonyl-L-methionyl-L-threonyl-L-methionyl-L-valyl-L-leucyl-L-seryl-L-phenylalanine (2R)-methylpyrrolidinyl amide (220052-64-2)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; trimethylpyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; 0 deg C, 1 h, room temperature, 2 h;

DOI:10.1016/S0968-0896(98)00162-X

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → Nα-9-fluorenylmethoxycarbonyl-L-methionyl-L-threonyl-L-methionyl-L-valyl-L-leucyl-L-seryl-L-phenylalanine (2R)-methylpyrrolidinyl amide (220052-64-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluorobirate / dimethylformamide / 5 h / Ambient temperature

2: 64 percent / iodine, triphenylphosphine, imidazole / toluene / 1.5 h / Ambient temperature

3: 93 percent / hydrogen, triethylamine / 10 percent Pd/C / ethyl acetate; ethanol / 1.17 h / 760 Torr

4: HCl / acetic acid / 1 h

5: 53 percent / HATU, HOAt, trimethylpyridine / dimethylformamide / 0 deg C, 1 h, room temperature, 2 h

With 1H-imidazole; hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; trimethylpyridine; hydrogen; iodine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In ethanol; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(98)00162-X

Reference yield:

Nα-tert-butoxycarbonyl-L-phenylalanine (2S)-hydroxymethylpyrrolidinyl amide (182815-41-4) → Nα-9-fluorenylmethoxycarbonyl-L-methionyl-L-threonyl-L-methionyl-L-valyl-L-leucyl-L-seryl-L-phenylalanine (2R)-methylpyrrolidinyl amide (220052-64-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / iodine, triphenylphosphine, imidazole / toluene / 1.5 h / Ambient temperature

2: 93 percent / hydrogen, triethylamine / 10 percent Pd/C / ethyl acetate; ethanol / 1.17 h / 760 Torr

3: HCl / acetic acid / 1 h

4: 53 percent / HATU, HOAt, trimethylpyridine / dimethylformamide / 0 deg C, 1 h, room temperature, 2 h

With 1H-imidazole; hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; trimethylpyridine; hydrogen; iodine; triethylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In ethanol; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(98)00162-X

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

N^α-tert-butoxycarbonyl-L-phenylalanine (2S)-hydroxymethylpyrrolidinyl amide

(S)-1-Pyrrolidin-2-yl-methanol

N^α-tert-butoxycarbonyl-L-phenylalanine (2R)-methylpyrrolidinyl amide

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