L-Leucine, N-[4-[[[(1S)-2-methoxy-1-methyl-2-oxoethyl](2-methylpropyl)amino]carb onyl]-2-(1-methylethoxy)benzoyl]-, methyl ester

Base Information

• Chemical Name: L-Leucine, N-[4-[[[(1S)-2-methoxy-1-methyl-2-oxoethyl](2-methylpropyl)amino]carb onyl]-2-(1-methylethoxy)benzoyl]-, methyl ester
• CAS No.: 681466-00-2
• Molecular Formula: C26H40N2O7
• Molecular Weight: 492.613
• Mol file: 681466-00-2.mol

Synonyms:

Chemical Property of L-Leucine, N-[4-[[[(1S)-2-methoxy-1-methyl-2-oxoethyl](2-methylpropyl)amino]carb onyl]-2-(1-methylethoxy)benzoyl]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Leucine, N-[4-[[[(1S)-2-methoxy-1-methyl-2-oxoethyl](2-methylpropyl)amino]carb onyl]-2-(1-methylethoxy)benzoyl]-, methyl ester

There total 12 articles about L-Leucine, N-[4-[[[(1S)-2-methoxy-1-methyl-2-oxoethyl](2-methylpropyl)amino]carb onyl]-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:

(S)-2-isobutylaminopropionic acid methyl ester (19648-66-9,198630-68-1) → (S)-2-{4-[isobutyl-((S)-1-methoxycarbonylethyl)carbamoyl]-2-isopropoxybenzoylamino}-4-methylpentanoic acid methyl ester (681466-00-2)

Guidance literature:

Multi-step reaction with 5 steps

1: CH₂Cl₂

2: OsO₄ / 2-methyl-propan-2-ol; CCl₄; H₂O

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

4: pyridinium dichromate / dimethylformamide

5: 1-hydroxybenzotriazole hydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl

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

DOI:10.1021/ja0446404

Reference yield:

3-hydroxy-4-aminobenzoic acid methyl ester (63435-16-5) → (S)-2-{4-[isobutyl-((S)-1-methoxycarbonylethyl)carbamoyl]-2-isopropoxybenzoylamino}-4-methylpentanoic acid methyl ester (681466-00-2)

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: CH₂Cl₂

7.1: OsO₄ / 2-methyl-propan-2-ol; CCl₄; H₂O

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

9.1: pyridinium dichromate / dimethylformamide

10.1: 1-hydroxybenzotriazole hydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl

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; 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-[isobutyl-((S)-1-methoxycarbonylethyl)carbamoyl]-2-isopropoxybenzoylamino}-4-methylpentanoic acid methyl ester (681466-00-2)

Guidance literature:

Multi-step reaction with 5 steps

1: CH₂Cl₂

2: OsO₄ / 2-methyl-propan-2-ol; CCl₄; H₂O

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

4: pyridinium dichromate / dimethylformamide

5: 1-hydroxybenzotriazole hydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl

With sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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

N-isobutyl-2-isopropoxy-N-(1-methoxycarbonyl-ethyl)-terephthalamic acid

methyl (L)-leucinate hydrochloride

(S)-2-isobutylaminopropionic acid methyl ester