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

Base Information

• Chemical Name: N^α-tert-butoxycarbonyl-L-phenylalanine (2S)-hydroxymethylpyrrolidinyl amide
• CAS No.: 182815-41-4
• Molecular Formula: C₁₉H₂₈N₂O₄
• Molecular Weight: 348.442
• Mol file: 182815-41-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about N^α-tert-butoxycarbonyl-L-phenylalanine (2S)-hydroxymethylpyrrolidinyl 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: 77.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → Nα-tert-butoxycarbonyl-L-phenylalanine (2S)-hydroxymethylpyrrolidinyl amide (182815-41-4)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; for 5h; Ambient temperature;

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

Reference yield: 64.0%

Nα-tert-butoxycarbonyl-L-phenylalanine (2S)-hydroxymethylpyrrolidinyl amide (182815-41-4) → Nα-tert-butoxycarbonyl-L-phenylalanine (2S)-iodomethylpyrrolidinyl amide (220052-61-9)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; for 1.5h; Ambient temperature;

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

Reference yield:

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

Guidance literature:

Multi-step reaction with 5 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

5: 26 percent / piperidine / dimethylformamide / 1 h / Ambient temperature

With piperidine; 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

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

Downstream raw materials:

N-(N-(3-phenoxybenzoyl)-L-phenylalanyl)-L-prolinol

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

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

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