L-Leucine, N-[4-[[bis(1-methylethyl)amino]carbonyl]-2-(1-methylethoxy)benzoyl]-, methyl ester

Base Information

• Chemical Name: L-Leucine, N-[4-[[bis(1-methylethyl)amino]carbonyl]-2-(1-methylethoxy)benzoyl]-, methyl ester
• CAS No.: 681465-54-3
• Molecular Formula: C24H38N2O5
• Molecular Weight: 434.576
• Mol file: 681465-54-3.mol

Synonyms:

Chemical Property of L-Leucine, N-[4-[[bis(1-methylethyl)amino]carbonyl]-2-(1-methylethoxy)benzoyl]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Leucine, N-[4-[[bis(1-methylethyl)amino]carbonyl]-2-(1-methylethoxy)benzoyl]-, methyl ester

There total 11 articles about L-Leucine, N-[4-[[bis(1-methylethyl)amino]carbonyl]-2-(1-methylethoxy)benzoyl]-, methyl ester 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: 85.0%

methyl (L)-leucinate hydrochloride (7517-19-3) + 2-isopropoxy-N,N-diisopropylterephthalamic acid (681465-93-0) → (S)-2-(4-diisopropylcarbamoyl-2-isopropoxybenzoylamino)-4-methylpentanoic acid methyl ester (681465-54-3)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/ja0446404

Reference yield:

3-hydroxy-4-aminobenzoic acid methyl ester (63435-16-5) → (S)-2-(4-diisopropylcarbamoyl-2-isopropoxybenzoylamino)-4-methylpentanoic acid methyl ester (681465-54-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 90 percent / Cs₂CO₃ / acetone / 10 h / Heating

2.1: aq. H₂SO₄; NaNO₂ / methanol / 0.25 h / 0 °C

2.2: 86 percent / KI; Cu / methanol / 8 h / Heating

3.1: 95 percent / Pd(PPh₃)4 / toluene / 12 h / Heating

4.1: aq. NaOH / methanol / 20 °C

5.1: oxalyl chloride; DMF / CH₂Cl₂ / 2 h / 20 °C

6.1: 2.04 g / CH₂Cl₂ / 3 h / 20 °C

7.1: OsO₄ / 2-methyl-propan-2-ol; CCl₄; H₂O / 0.25 h / 20 °C

8.1: NaIO₄ / 2-methyl-propan-2-ol; CCl₄; H₂O

9.1: 187.3 mg / pyridinium dichromate / dimethylformamide / 6 h / 20 °C

10.1: 85 percent / 1-hydroxybenzotriazole hydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; Et₃N / CH₂Cl₂ / 24 h / 20 °C

With sodium hydroxide; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; sulfuric acid; caesium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-dimethyl-formamide; sodium nitrite; In methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 2.2: Sandmeyer reaction / 3.1: Stille coupling / 9.1: Corey-Schmidt oxidation;

DOI:10.1021/ja0446404

Reference yield:

3-isopropoxy-4-vinylbenzoic acid chloride → (S)-2-(4-diisopropylcarbamoyl-2-isopropoxybenzoylamino)-4-methylpentanoic acid methyl ester (681465-54-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.04 g / CH₂Cl₂ / 3 h / 20 °C

2: OsO₄ / 2-methyl-propan-2-ol; CCl₄; H₂O / 0.25 h / 20 °C

3: NaIO₄ / 2-methyl-propan-2-ol; CCl₄; H₂O

4: 187.3 mg / pyridinium dichromate / dimethylformamide / 6 h / 20 °C

5: 85 percent / 1-hydroxybenzotriazole hydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; Et₃N / CH₂Cl₂ / 24 h / 20 °C

With sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 4: Corey-Schmidt oxidation;

DOI:10.1021/ja0446404

upstream raw materials:

(S)-Leu-OMe

2-isopropoxy-N,N-diisopropylterephthalamic acid

methyl (L)-leucinate hydrochloride

3-hydroxy-4-aminobenzoic acid methyl ester