N⁶-(tert-butoxycarbonyl)-N²-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester

Base Information

• Chemical Name: N⁶-(tert-butoxycarbonyl)-N²-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester
• CAS No.: 120095-49-0
• Molecular Formula: C₃₂H₅₁N₃O₇
• Molecular Weight: 589.773
• Mol file: 120095-49-0.mol

Synonyms:N⁶-(tert-butoxycarbonyl)-N²-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester

Chemical Property of N⁶-(tert-butoxycarbonyl)-N²-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-(tert-butoxycarbonyl)-N²-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester

There total 6 articles about N⁶-(tert-butoxycarbonyl)-N²-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline 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: 70.0%

L-Lys(Boc)-L-Pro-OBut (32489-85-3) + (R)-ethyl 2-bromo-4-phenylbutyrate (121842-77-1) → N6-(tert-butoxycarbonyl)-N2-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester (120095-49-0)

Guidance literature:

With ammonium carbonate; In nitromethane; water; at 50 ℃; for 96h;

DOI:10.1248/cpb.37.280

Reference yield:

3-phenyl-propionaldehyde (104-53-0) → N6-(tert-butoxycarbonyl)-N2-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester (120095-49-0)

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: 70 percent / (NH₄)2CO₃ / H₂O; nitromethane / 96 h / 50 °C

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

DOI:10.1248/cpb.37.280

Reference yield:

5-phenylethyl-imidazolidine-2,4-dione (120379-81-9) → N6-(tert-butoxycarbonyl)-N2-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester (120095-49-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 99.3 percent / NH₄Cl / aq. NH₃ / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9

2: 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

3: 95 percent / SOCl₂ / 24 h / Ambient temperature

4: 70 percent / (NH₄)2CO₃ / H₂O; nitromethane / 96 h / 50 °C

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

DOI:10.1248/cpb.37.280

upstream raw materials:

Diazoethan

2-oxo-4-phenylbutyric acid

L-Lys(Boc)-L-Pro-OBu^t

(R)-ethyl 2-bromo-4-phenylbutyrate

Downstream raw materials:

N²-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline

Lisinopril

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.