N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester

Base Information

• Chemical Name: N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester
• CAS No.: 80828-38-2
• Molecular Formula: C₁₉H₂₉NO₄
• Molecular Weight: 335.444
• Mol file: 80828-38-2.mol

Synonyms:N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester

Chemical Property of N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester

There total 7 articles about N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester 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: 31.0%

2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2) + L-alanine tert butyl ester (105259-95-8) → N-<(R)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester (80828-28-0) + N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester (80828-38-2)

Guidance literature:

With sodium acetate; sodium cyanoborohydride; acetic acid; In ethanol; for 5h;

DOI:10.1248/cpb.34.2852

Reference yield: 9.2%

tert-butyl L-alaninate hydrochloride (13404-22-3) + (R)-ethyl 2-bromo-4-phenylbutyrate (121842-77-1) → N-<(R)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester (80828-28-0) + N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester (80828-38-2)

Guidance literature:

With ammonium carbonate; In nitromethane; water; at 50 ℃; for 4h;

DOI:10.1248/cpb.37.280

Reference yield:

3-phenyl-propionaldehyde (104-53-0) → N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester (80828-38-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 45 percent / methanol; H₂O / 8 h / 70 °C

2: 99.3 percent / NH₄Cl / aq. NH₃ / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9

3: 1.) NaNO₂, 2N H₂SO₄; 2.) KBr, NaNO₂, 3N H₂SO₄ / 1.) 50percent CH₃COOH, r.t., 24 h; 2.) 50percent CH₃COOH, 0-5 deg C, 1 h

4: 95 percent / SOCl₂ / 24 h / Ambient temperature

5: H₂O; nitromethane / 72 h / 50 °C / examined various solvent-base systems

With thionyl chloride; sulfuric acid; ammonium chloride; potassium bromide; sodium nitrite; In methanol; ammonium hydroxide; nitromethane; water;

DOI:10.1248/cpb.37.280

upstream raw materials:

Diazoethan

2-oxo-4-phenylbutyric acid

tert-butyl L-alaninate hydrochloride

2-oxo-4-phenylbutanoic acid ethyl ester

Downstream raw materials:

N-(2,3-dihydro-1H-inden-2-yl)-N--L-alanyl>-glycine t-butyl ester

N--L-alanyl>-L-proline tert butyl ester

Delaprilat

delapril hydrochloride

Refernces

• 1、 Iwasaki, Genji,Kimura, Rieko,Numao, Naganori,Kondo, Kiyoshi. "A Stereoselective Synthesis of N--L-alanine Derivatives by Means of Reductive Amination". . p. 1691 - 1694. Retrieved 2007/10/02.