1-Methyl N-(N-formyl-L-alpha-aspartyl)-3-phenyl-L-alaninate

Base Information

• Chemical Name: 1-Methyl N-(N-formyl-L-alpha-aspartyl)-3-phenyl-L-alaninate
• CAS No.: 33605-76-4
• Molecular Formula: C15H18N2O6
• Molecular Weight: 322.318
• European Community (EC) Number: 251-590-3
• DSSTox Substance ID: DTXSID50955238
• Mol file: 33605-76-4.mol

Synonyms:1-Methyl N-(N-formyl-L-alpha-aspartyl)-3-phenyl-L-alaninate;3-formamido-4-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino]-4-oxobutanoic acid;33605-76-4;EINECS 251-590-3;SCHEMBL7030032;DTXSID50955238;4-Hydroxy-3-[(hydroxymethylidene)amino]-4-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)imino]butanoic acid

Chemical Property of 1-Methyl N-(N-formyl-L-alpha-aspartyl)-3-phenyl-L-alaninate

Chemical Property:

• Melting Point: 138-141℃
• Boiling Point: 643.513 °C at 760 mmHg
• Flash Point: 342.985 °C
• PSA: 121.80000
• Density: 1.296 g/cm³
• LogP: 0.89390
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 322.11648630
• Heavy Atom Count: 23
• Complexity: 434

Purity/Quality:

99% ^*data from raw suppliers

FOR-ASP-PHE-OME 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O)NC=O

Technology Process of 1-Methyl N-(N-formyl-L-alpha-aspartyl)-3-phenyl-L-alaninate

There total 7 articles about 1-Methyl N-(N-formyl-L-alpha-aspartyl)-3-phenyl-L-alaninate 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: 100.0%

→ N-formylaspartame (33605-76-4)

Guidance literature:

Reference yield: 65.5%

n-formyl-l-aspartic anhydride (116147-62-7) + methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → N-formylaspartame (33605-76-4)

Guidance literature:

With sodium acetate; acetic acid; In ethyl acetate;

Reference yield:

(Z)-N-(N-formyl-α-L-aspartyl)-Δ-phenylalanine methyl ester (100101-47-1) → N-formylaspartame (33605-76-4) + (S)-3-Formylamino-N-((R)-1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid (99792-97-9)

Guidance literature:

With hydrogen; Rh-(R)-prophos; In tetrahydrofuran; at 23 ℃; under 760 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00357a036

upstream raw materials:

N-(2,5-Dioxo-tetrahydro-furan-3-yl)-formamide

L-phenylalanine methyl ester

(Z)-N-(N-formyl-α-L-aspartyl)-Δ-phenylalanine methyl ester

N-formyl-L-aspartic acid

Downstream raw materials:

L-Asp-L-Phe-OMe

α-L-aspartyl-L-phenylalanine methyl ester hydrochloride

Refernces

• 1、 -. "Preparation of N-protected α-L-aspartyl-L-phenylalanine methyl ester". . . Retrieved 2008/06/13.
• 2、 Fuganti, Claudio,Grasselli, Piero,Malpezzi, Luciana. "Synthesis of Aspartame via Asymmetric Hydrogenation of N-Protected (Z)-N-α-L-Aspartyl-Δ-phenylalanine Methyl Ester". . p. 1126 - 1128. Retrieved 2007/10/02.