N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl-DL-α-acetoxy)glycinamide

Base Information

• Chemical Name: N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl-DL-α-acetoxy)glycinamide
• CAS No.: 271581-18-1
• Molecular Formula: C₂₅H₃₁N₃O₆
• Molecular Weight: 469.538
• Mol file: 271581-18-1.mol

Synonyms:N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl-DL-α-acetoxy)glycinamide

Chemical Property of N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl-DL-α-acetoxy)glycinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl-DL-α-acetoxy)glycinamide

There total 4 articles about N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl-DL-α-acetoxy)glycinamide 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: 96.0%

lead(IV) tetraacetate (546-67-8) + N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl)-L-serinamide (271581-17-0) → N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl-DL-α-acetoxy)glycinamide (271581-18-1)

Guidance literature:

With 4 A molecular sieve; In ethyl acetate; for 2h; Heating;

DOI:10.1039/a907483j

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl-DL-α-acetoxy)glycinamide (271581-18-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / BOP; Et₃N / CH₂Cl₂ / 20 °C

2: 100 percent / NaOH; water / methanol / 3 h

3: 96 percent / BOP; Et₃N / CH₂Cl₂ / 20 °C

4: 96 percent / 4 Angstroem molecular sieves / ethyl acetate / 2 h / Heating

With sodium hydroxide; 4 A molecular sieve; water; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In methanol; dichloromethane; ethyl acetate; 1: Acylation / 2: Hydrolysis / 3: Acylation / 4: Acetylation;

DOI:10.1039/a907483j

Reference yield:

(S)-2-((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid (123228-32-0) → N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl-DL-α-acetoxy)glycinamide (271581-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / BOP; Et₃N / CH₂Cl₂ / 20 °C

2: 96 percent / 4 Angstroem molecular sieves / ethyl acetate / 2 h / Heating

With 4 A molecular sieve; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane; ethyl acetate; 1: Acylation / 2: Acetylation;

DOI:10.1039/a907483j

upstream raw materials:

lead(IV) tetraacetate

N-Benzyl-(N-tert-butyloxycarbonyl-L-phenylalanyl)-L-serinamide

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-((S)-2-(((tert-butoxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoic acid