N-[trans-4-(2-hydroxy-1-methylethyl)cyclohexanecarbonyl]-D-phenylalanine

Base Information

• Chemical Name: N-[trans-4-(2-hydroxy-1-methylethyl)cyclohexanecarbonyl]-D-phenylalanine
• CAS No.: 183996-83-0
• Molecular Formula: C₁₉H₂₇NO₄
• Molecular Weight: 333.428
• Mol file: 183996-83-0.mol

Synonyms:N-[trans-4-(2-hydroxy-1-methylethyl)cyclohexanecarbonyl]-D-phenylalanine

Chemical Property of N-[trans-4-(2-hydroxy-1-methylethyl)cyclohexanecarbonyl]-D-phenylalanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[trans-4-(2-hydroxy-1-methylethyl)cyclohexanecarbonyl]-D-phenylalanine

There total 5 articles about N-[trans-4-(2-hydroxy-1-methylethyl)cyclohexanecarbonyl]-D-phenylalanine 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: 49.0%

(R)-2-{[4-(2-Hydroxy-1-methyl-ethyl)-cyclohexanecarbonyl]-amino}-3-phenyl-propionic acid benzyl ester → N-[trans-4-(2-hydroxy-1-methylethyl)cyclohexanecarbonyl]-D-phenylalanine (183996-83-0)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/0968-0896(96)00187-3

Reference yield:

trans-1-chlorocarbonyl-4-(methoxycarbonyl)-cyclohexane (32529-80-9,36218-60-7) → N-[trans-4-(2-hydroxy-1-methylethyl)cyclohexanecarbonyl]-D-phenylalanine (183996-83-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) CuI / 1.) Et₂O, THF, 2 h, 2.) Et₂O, THF, 30 min

2: 1.) Zn, TiCl₄ / 1.) THF, 5 deg C, 4 d, 4.) THF, CH₂Cl₂, RT, 3.5 h

3: 1.) BH₃-THF, 2.) aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h

4: 93 percent / aq. NaOH / methanol; acetone / Ambient temperature

5: 90 percent / DCC, HOBt / CH₂Cl₂; tetrahydrofuran

6: 49 percent / H₂ / 10percent Pd/C

With sodium hydroxide; copper(l) iodide; borane-THF; hydrogen; dihydrogen peroxide; titanium tetrachloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1016/0968-0896(96)00187-3

Reference yield:

trans-4-acetylcyclohexanecarboxylic acid methyl ester (183996-94-3) → N-[trans-4-(2-hydroxy-1-methylethyl)cyclohexanecarbonyl]-D-phenylalanine (183996-83-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Zn, TiCl₄ / 1.) THF, 5 deg C, 4 d, 4.) THF, CH₂Cl₂, RT, 3.5 h

2: 1.) BH₃-THF, 2.) aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h

3: 93 percent / aq. NaOH / methanol; acetone / Ambient temperature

4: 90 percent / DCC, HOBt / CH₂Cl₂; tetrahydrofuran

5: 49 percent / H₂ / 10percent Pd/C

With sodium hydroxide; borane-THF; hydrogen; dihydrogen peroxide; titanium tetrachloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1016/0968-0896(96)00187-3

upstream raw materials:

trans-1-chlorocarbonyl-4-(methoxycarbonyl)-cyclohexane

trans-4-acetylcyclohexanecarboxylic acid methyl ester

4-Isopropenyl-cyclohexanecarboxylic acid methyl ester