(R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-oxoethyl>-N²--L-phenylalanyl>-L-leucinamide

Base Information

• Chemical Name: (R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-oxoethyl>-N²--L-phenylalanyl>-L-leucinamide
• CAS No.: 151521-04-9
• Molecular Formula: C₂₉H₄₅N₃O₆
• Molecular Weight: 531.693

Synonyms:(R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-oxoethyl>-N²--L-phenylalanyl>-L-leucinamide

Chemical Property of (R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-oxoethyl>-N²--L-phenylalanyl>-L-leucinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-oxoethyl>-N²--L-phenylalanyl>-L-leucinamide

There total 5 articles about (R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-oxoethyl>-N²--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: 96.5%

(R*)-N-<1-(cyclohexylmethyl)-2-methoxy-2-oxoethyl>-N2--L-phenylalanyl>-L-leucinamide (151521-03-8) → (R*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-oxoethyl>-N2--L-phenylalanyl>-L-leucinamide (151521-04-9)

Guidance literature:

With sodium hydroxide; In methanol; for 1h; Heating;

DOI:10.1021/jm00069a001

Reference yield:

(S)-Leu-OMe (2666-93-5) → (R*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-oxoethyl>-N2--L-phenylalanyl>-L-leucinamide (151521-04-9)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jm00069a001

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (R*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-oxoethyl>-N2--L-phenylalanyl>-L-leucinamide (151521-04-9)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jm00069a001

upstream raw materials:

(R^*)-N-<1-(cyclohexylmethyl)-2-methoxy-2-oxoethyl>-N²--L-phenylalanyl>-L-leucinamide

(S)-Leu-OMe

N-tert-butoxycarbonyl-L-phenylalanine

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

Downstream raw materials:

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

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