2-[(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-2-oxo-4-phenyl-butyl]-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-[(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-2-oxo-4-phenyl-butyl]-malonic acid dimethyl ester
• CAS No.: 196957-53-6
• Molecular Formula: C₂₆H₃₀N₂O₈
• Molecular Weight: 498.533

Synonyms:2-[(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-2-oxo-4-phenyl-butyl]-malonic acid dimethyl ester

Chemical Property of 2-[(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-2-oxo-4-phenyl-butyl]-malonic acid dimethyl ester

Chemical Property:

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Technology Process of 2-[(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-2-oxo-4-phenyl-butyl]-malonic acid dimethyl ester

There total 2 articles about 2-[(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-2-oxo-4-phenyl-butyl]-malonic acid dimethyl 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: 72.0%

dimethyl malonate sodium salt (18424-76-5) + Z-Ala-PheCH2Cl (26049-92-3) → 2-[(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-2-oxo-4-phenyl-butyl]-malonic acid dimethyl ester (196957-53-6)

Guidance literature:

With sodium iodide; In tetrahydrofuran; Ambient temperature;

DOI:10.3987/com-97-7859

Reference yield:

N-benzyloxycarbonyl-L-alanyl-L-phenylalanine (2768-53-8) → 2-[(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-2-oxo-4-phenyl-butyl]-malonic acid dimethyl ester (196957-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) N-methylmorpholine, isobutyl chloroformate; 3.) 2N HCl / 1.) THF, -20 deg C, 15 min; 2.) THF, ether, 30 min; 3.) THF, ether, MeOH

2: 72 percent / 1.) sodium iodide / tetrahydrofuran / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium iodide; isobutyl chloroformate; In tetrahydrofuran;

DOI:10.3987/com-97-7859

Reference yield: 81.0%

2-[(S)-3-((S)-2-Benzyloxycarbonylamino-propionylamino)-2-oxo-4-phenyl-butyl]-malonic acid dimethyl ester (196957-53-6) → 2-((3S,6S)-3-Benzyl-6-methyl-5-oxo-3,4,5,6-tetrahydro-pyrazin-2-ylmethyl)-malonic acid dimethyl ester

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 23 ℃; for 2h;

DOI:10.1016/S0968-0896(97)00026-6

upstream raw materials:

dimethyl malonate sodium salt

Z-Ala-PheCH₂Cl

N-benzyloxycarbonyl-L-alanyl-L-phenylalanine

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