(S)-2-[((S)-4-Methyl-2-phenyl-4,5-dihydro-oxazole-4-carbonyl)-amino]-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-[((S)-4-Methyl-2-phenyl-4,5-dihydro-oxazole-4-carbonyl)-amino]-propionic acid benzyl ester
• CAS No.: 177762-99-1
• Molecular Formula: C₂₁H₂₂N₂O₄
• Molecular Weight: 366.417
• Mol file: 177762-99-1.mol

Synonyms:(S)-2-[((S)-4-Methyl-2-phenyl-4,5-dihydro-oxazole-4-carbonyl)-amino]-propionic acid benzyl ester

Chemical Property of (S)-2-[((S)-4-Methyl-2-phenyl-4,5-dihydro-oxazole-4-carbonyl)-amino]-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[((S)-4-Methyl-2-phenyl-4,5-dihydro-oxazole-4-carbonyl)-amino]-propionic acid benzyl ester

There total 5 articles about (S)-2-[((S)-4-Methyl-2-phenyl-4,5-dihydro-oxazole-4-carbonyl)-amino]-propionic acid benzyl 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: 92.0%

L-alanine benzyl ester hydrochloride (5557-81-3,5557-83-5,34404-37-0) + (R)-4-Bromomethyl-4-methyl-2-phenyl-4H-oxazol-5-one (177762-93-5) → (S)-2-[((S)-4-Methyl-2-phenyl-4,5-dihydro-oxazole-4-carbonyl)-amino]-propionic acid benzyl ester (177762-99-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 50 ℃; for 17h;

DOI:10.1021/jo952068g

Reference yield:

2-phenyl-4-methyl-4H-oxazolin-5-one (51127-13-0,71963-72-9,87480-74-8,13302-43-7) → (S)-2-[((S)-4-Methyl-2-phenyl-4,5-dihydro-oxazole-4-carbonyl)-amino]-propionic acid benzyl ester (177762-99-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 34 percent / NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C

2: 48 percent / DIPEA, NMP / 18 h / 55 °C

3: 75 percent / HBr/AcOH / acetic anhydride / 5 h / 80 °C

4: 92 percent / DIPEA / N,N-dimethyl-acetamide / 17 h / 50 °C

With 1-methyl-pyrrolidin-2-one; hydrogen bromide; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl acetamide; acetic anhydride; N,N-dimethyl-formamide;

DOI:10.1021/jo952068g

Reference yield:

N-Benzoylalanine (2198-64-3,1205-02-3,90988-29-7) → (S)-2-[((S)-4-Methyl-2-phenyl-4,5-dihydro-oxazole-4-carbonyl)-amino]-propionic acid benzyl ester (177762-99-1)

Guidance literature:

Multi-step reaction with 5 steps

1: DCC / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temperature, 40 min

2: 34 percent / NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C

3: 48 percent / DIPEA, NMP / 18 h / 55 °C

4: 75 percent / HBr/AcOH / acetic anhydride / 5 h / 80 °C

5: 92 percent / DIPEA / N,N-dimethyl-acetamide / 17 h / 50 °C

With 1-methyl-pyrrolidin-2-one; hydrogen bromide; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; acetic anhydride; N,N-dimethyl-formamide;

DOI:10.1021/jo952068g

upstream raw materials:

L-alanine benzyl ester hydrochloride

(R)-4-Bromomethyl-4-methyl-2-phenyl-4H-oxazol-5-one

2-phenyl-4-methyl-4H-oxazolin-5-one

N-Benzoylalanine