2-azido-2-(3,5-bis-benzyloxy-4-methoxy-phenyl)-N-methyl-acetamide

Base Information

• Chemical Name: 2-azido-2-(3,5-bis-benzyloxy-4-methoxy-phenyl)-N-methyl-acetamide
• CAS No.: 299179-30-9
• Molecular Formula: C₂₄H₂₄N₄O₄
• Molecular Weight: 432.479
• Mol file: 299179-30-9.mol

Synonyms:2-azido-2-(3,5-bis-benzyloxy-4-methoxy-phenyl)-N-methyl-acetamide

Chemical Property of 2-azido-2-(3,5-bis-benzyloxy-4-methoxy-phenyl)-N-methyl-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-2-(3,5-bis-benzyloxy-4-methoxy-phenyl)-N-methyl-acetamide

There total 1 articles about 2-azido-2-(3,5-bis-benzyloxy-4-methoxy-phenyl)-N-methyl-acetamide 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: 91.0%

methylamine (74-89-5) + (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoic acid (191542-07-1) → 2-azido-2-(3,5-bis-benzyloxy-4-methoxy-phenyl)-N-methyl-acetamide (299179-30-9)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(00)00855-8

Reference yield:

2-azido-2-(3,5-bis-benzyloxy-4-methoxy-phenyl)-N-methyl-acetamide (299179-30-9) → 2-amino-2-(3,5-dihydroxy-4-methoxy-phenyl)-N-methyl-acetamide

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; for 12h;

DOI:10.1016/S0040-4039(00)00855-8

Reference yield:

2-azido-2-(3,5-bis-benzyloxy-4-methoxy-phenyl)-N-methyl-acetamide (299179-30-9) → (R)-2-[(S)-2-Amino-2-(3-hydroxy-5-methoxy-4-methyl-phenyl)-acetylamino]-2-(3,5-dihydroxy-4-methoxy-phenyl)-N-methyl-acetamide (1026383-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂; aq. HCl / Pd/C / methanol; tetrahydrofuran / 12 h / 760.05 Torr

2: 70 mg / HOAt; EDCI; TMP / CH₂Cl₂; dimethylformamide / 0 - 20 °C

3: H₂; aq. HCl / Pd/C / methanol; tetrahydrofuran / 20 h / 760.05 Torr

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; hydrogen; thymidine 5'-phosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Acylation / 3: Hydrogenolysis;

DOI:10.1021/ol000180h

upstream raw materials:

methylamine

(2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoic acid

Downstream raw materials:

(R)-2-[(S)-2-Amino-2-(3-hydroxy-5-methoxy-4-methyl-phenyl)-acetylamino]-2-(3,5-dihydroxy-4-methoxy-phenyl)-N-methyl-acetamide

N-methyl (2R)-2-[(S)-1-[((benzyloxy)carbonyl)amino]-1-(3-benzyloxy-5-methoxy-4-methylphenyl)methylcarboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanamide

((S)-{[(R)-(3,5-Dihydroxy-4-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-phenyl-methyl)-carbamic acid benzyl ester