N-[1-(cyclohexylmethyl)-3-ethoxy-2,3-dioxopropyl]-N²-{N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl}-L-leucinamide

Base Information

• Chemical Name: N-[1-(cyclohexylmethyl)-3-ethoxy-2,3-dioxopropyl]-N²-{N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl}-L-leucinamide
• CAS No.: 169529-75-3
• Molecular Formula: C₃₂H₄₉N₃O₇
• Molecular Weight: 587.757

Synonyms:N-[1-(cyclohexylmethyl)-3-ethoxy-2,3-dioxopropyl]-N²-{N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl}-L-leucinamide

Chemical Property of N-[1-(cyclohexylmethyl)-3-ethoxy-2,3-dioxopropyl]-N²-{N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl}-L-leucinamide

Chemical Property:

Purity/Quality:

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Technology Process of N-[1-(cyclohexylmethyl)-3-ethoxy-2,3-dioxopropyl]-N²-{N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl}-L-leucinamide

There total 7 articles about N-[1-(cyclohexylmethyl)-3-ethoxy-2,3-dioxopropyl]-N²-{N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl}-L-leucinamide 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:

C33H49N3O9 → N-[1-(cyclohexylmethyl)-3-ethoxy-2,3-dioxopropyl]-N2-{N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl}-L-leucinamide (169529-75-3)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; Yield given; Ambient temperature;

DOI:10.1021/jm00069a001

Reference yield:

(S)-Leu-OMe (2666-93-5) → N-[1-(cyclohexylmethyl)-3-ethoxy-2,3-dioxopropyl]-N2-{N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl}-L-leucinamide (169529-75-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 66.1 percent / DCC, HOBT, iPr₂NEt / tetrahydrofuran / 14 h / 0 - 20 °C

2: 99 percent / 1 N NaOH / methanol / 1 h

3: 1.) HOBt, 2.) iPr₂NEt, DCC / 1.) DMF, THF, 0 deg C, 2 min, 2.) DMF, THF, a) 0 deg C, 2 h, b) RT, overnight

4: 96.5 percent / 1 N NaOH / methanol / 1 h / Heating

5: 1.) DMAP, pyridine / 1.) THF, DMF, 5 min, 2.) THF, DMF, reflux, 2 h

6: NaHCO₃ / ethanol / Ambient temperature

With pyridine; dmap; sodium hydroxide; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol;

DOI:10.1021/jm00069a001

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → N-[1-(cyclohexylmethyl)-3-ethoxy-2,3-dioxopropyl]-N2-{N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl}-L-leucinamide (169529-75-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 66.1 percent / DCC, HOBT, iPr₂NEt / tetrahydrofuran / 14 h / 0 - 20 °C

2: 99 percent / 1 N NaOH / methanol / 1 h

3: 1.) HOBt, 2.) iPr₂NEt, DCC / 1.) DMF, THF, 0 deg C, 2 min, 2.) DMF, THF, a) 0 deg C, 2 h, b) RT, overnight

4: 96.5 percent / 1 N NaOH / methanol / 1 h / Heating

5: 1.) DMAP, pyridine / 1.) THF, DMF, 5 min, 2.) THF, DMF, reflux, 2 h

6: NaHCO₃ / ethanol / Ambient temperature

With pyridine; dmap; sodium hydroxide; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol;

DOI:10.1021/jm00069a001

upstream raw materials:

(S)-Leu-OMe

N-tert-butoxycarbonyl-L-phenylalanine

methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-4-methylpentanoate

tert-butoxycarbonyl-L-phenylalanyl-L-leucine

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