(benzyloxycarbonyl)-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester

Base Information

• Chemical Name: (benzyloxycarbonyl)-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester
• CAS No.: 321983-69-1
• Molecular Formula: C₂₅H₃₀N₂O₅
• Molecular Weight: 438.524
• Mol file: 321983-69-1.mol

Synonyms:(benzyloxycarbonyl)-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester

Chemical Property of (benzyloxycarbonyl)-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (benzyloxycarbonyl)-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester

There total 1 articles about (benzyloxycarbonyl)-L-phenylalanine-piperidine-3R-carboxylic acid ethyl 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: 77.0%

N-Cbz-L-Phe (1161-13-3) + (R)-3-piperidinecarboxylic acid ethyl ester (+)-tartrate (163343-71-3,83602-38-4) → (benzyloxycarbonyl)-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester (321983-69-1)

Guidance literature:

N-Cbz-L-Phe; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -15 ℃; for 0.5h;

(R)-3-piperidinecarboxylic acid ethyl ester (+)-tartrate; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; Further stages.;

DOI:10.1021/jo001296u

Reference yield:

(benzyloxycarbonyl)-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester (321983-69-1) → (R)-1-((S)-2-Amino-3-phenyl-propionyl)-piperidine-3-carboxylic acid ethyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1021/jo001296u

Reference yield:

(benzyloxycarbonyl)-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester (321983-69-1) → (Z)-(3S,6S,21R)-3-Benzyl-6-isopropyl-19-oxa-1,4,7-triaza-bicyclo[19.3.1]pentacos-13-ene-2,5,8,20-tetraone

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd/C / ethanol

2: 21.0 g / EDC; HOBT / tetrahydrofuran / 20 °C

3: H₂ / Pd/C / ethanol

4: EDC; HOBT / tetrahydrofuran / 20 °C

5: aq. LiOH / tetrahydrofuran / 20 °C

6: DCC; DMAP / CH₂Cl₂ / 20 °C

7: PhC=RuCl₂(PCy₃)2 / CH₂Cl₂ / Heating

With dmap; lithium hydroxide; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo001296u

upstream raw materials:

N-Cbz-L-Phe

(R)-3-piperidinecarboxylic acid ethyl ester (+)-tartrate

Downstream raw materials:

(benzyloxycarbonyl)-L-valine-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester

hept-6-en-1-oyl-L-valine-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester

hept-6-en-1-oyl-L-valine-L-phenylalanine-piperidine-3R-carboxylic acid hexa-3,5-dienyl ester

hept-6-en-1-oyl-L-valine-L-phenylalanine-piperidine-3R-carboxylic acid hex-5-enyl ester