benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoate

Base Information

• Chemical Name: benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoate
• CAS No.: 376648-82-7
• Molecular Formula: C₁₉H₂₅F₃N₂O₅
• Molecular Weight: 418.413

Synonyms:benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoate

Chemical Property of benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoate

Chemical Property:

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Technology Process of benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoate

There total 3 articles about benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoate 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: 94.15%

(2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoic acid (63865-89-4) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoate (376648-82-7)

Guidance literature:

(2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoic acid; benzyl chloroformate; With 4-methyl-morpholine; In tetrahydrofuran; at -15 - 0 ℃; for 0.283333h;

With dmap; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield:

Boc-Orn(Z)-OH (2480-93-5) → benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoate (376648-82-7)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/C / methanol / 12 h / 20 °C / 760.05 Torr

2: Et₃N / methanol / 9 h

3: 89 percent / N-methylmorpholine; DMAP / tetrahydrofuran / -15 - 20 °C

With 4-methyl-morpholine; dmap; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/ol0161108

Reference yield:

N2-(tert-butoxycarbonyl)-L-ornithine (21887-64-9) → benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoate (376648-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / methanol / 9 h

2: 89 percent / N-methylmorpholine; DMAP / tetrahydrofuran / -15 - 20 °C

With 4-methyl-morpholine; dmap; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1021/ol0161108

upstream raw materials:

(2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanoic acid

benzyl chloroformate

Boc-Orn(Z)-OH

N₂-(tert-butoxycarbonyl)-L-ornithine

Downstream raw materials:

2-[2-[2-[2-tert-butoxycarbonylamino-5-(2,2,2-trifluoro-acetylamino)-pentanoylamino]-5-(2,2,2-trifluoro-acetylamino)-pentanoylamino]-5-(2,2,2-trifluoro-acetylamino)-pentanoylamino]-5-(2,2,2-trifluoro-acetylamino)-pentanoic acid benzyl ester

benzyl (2S)-2-[(2S)-2-[(tert-butoxycarbonyl)amino]-5-(2,2,2-trifluoroacetamido)pentanamido]-5-(2,2,2-trifluoroacetamido)pentanoate

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