diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate

Base Information

• Chemical Name: diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate
• CAS No.: 303174-07-4
• Molecular Formula: C₁₇H₂₈NO₅P
• Molecular Weight: 357.387
• Mol file: 303174-07-4.mol

Synonyms:diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate

Chemical Property of diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate

There total 2 articles about diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate 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: 68.0%

di-tert-butyl dicarbonate (24424-99-5) + diethyl N-(4-methylphenyl)methylphosphoramidate (303174-10-9) → diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate (303174-07-4)

Guidance literature:

diethyl N-(4-methylphenyl)methylphosphoramidate; With lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.166667h;

di-tert-butyl dicarbonate; In tetrahydrofuran; at -78 - 20 ℃; for 16h; Further stages.;

DOI:10.1021/jo000585f

Reference yield:

para-methylbenzylamine (104-84-7) → diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate (303174-07-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

2.1: LDA / tetrahydrofuran; cyclohexane / 0.17 h / -78 °C

2.2: 68 percent / tetrahydrofuran / 16 h / -78 - 20 °C

With triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; 1.1: Substitution / 2.1: Metallation / 2.2: Substitution;

DOI:10.1021/jo000585f

Reference yield:

diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate (303174-07-4) → (tert-butoxycarbonylamino-p-tolyl-methyl)-phosphonic acid diethyl ester (303174-05-2)

Guidance literature:

diethyl N-tert-butoxycarbonyl-N-(4-methylphenyl)methylphosphoramidate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at -78 ℃; for 0.5h;

With acetic acid; In diethyl ether; Further stages.;

DOI:10.1021/jo000585f

upstream raw materials:

di-tert-butyl dicarbonate

diethyl N-(4-methylphenyl)methylphosphoramidate

para-methylbenzylamine

Downstream raw materials:

(tert-butoxycarbonylamino-p-tolyl-methyl)-phosphonic acid diethyl ester