2,2,2-trichloro-tert-butyl N-{3-azido-N-[3-(p-tolylsulfonyloxy)-propyl]-prop-1-yl}carbamate

Base Information

Chemical Name:2,2,2-trichloro-tert-butyl N-{3-azido-N-[3-(p-tolylsulfonyloxy)-propyl]-prop-1-yl}carbamate
CAS No.:217454-40-5
Molecular Formula:C₁₈H₂₅Cl₃N₄O₅S
Molecular Weight:515.845
Hs Code.:

Synonyms:2,2,2-trichloro-tert-butyl N-{3-azido-N-[3-(p-tolylsulfonyloxy)-propyl]-prop-1-yl}carbamate

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Chemical Property of 2,2,2-trichloro-tert-butyl N-{3-azido-N-[3-(p-tolylsulfonyloxy)-propyl]-prop-1-yl}carbamate

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Technology Process of 2,2,2-trichloro-tert-butyl N-{3-azido-N-[3-(p-tolylsulfonyloxy)-propyl]-prop-1-yl}carbamate

There total 2 articles about 2,2,2-trichloro-tert-butyl N-{3-azido-N-[3-(p-tolylsulfonyloxy)-propyl]-prop-1-yl}carbamate 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: 70.0%

: 98-59-9
p-toluenesulfonyl chloride

: 217454-51-8
2,2,2-trichloro-tert-butyl N-[3-azido-N-(3-hydroxypropyl)-prop-1-yl]carbamate

: 217454-40-5
2,2,2-trichloro-tert-butyl N-{3-azido-N-[3-(p-tolylsulfonyloxy)-propyl]-prop-1-yl}carbamate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 25.5h;
DOI:10.1021/jo980689e

Reference yield:

: 217454-49-4
3-<(3-azidopropyl)amino>propan-1-ol

: 217454-40-5
2,2,2-trichloro-tert-butyl N-{3-azido-N-[3-(p-tolylsulfonyloxy)-propyl]-prop-1-yl}carbamate

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / aq. NaOH / diethyl ether / 1.5 h / 0 °C

2: 70 percent / DMAP; Et₃N / CH₂Cl₂ / 25.5 h / 0 - 20 °C

With dmap; sodium hydroxide; triethylamine; In diethyl ether; dichloromethane; 1: Acylation / 2: Tosylation;
DOI:10.1021/jo980689e

Reference yield:

: 217454-40-5
2,2,2-trichloro-tert-butyl N-{3-azido-N-[3-(p-tolylsulfonyloxy)-propyl]-prop-1-yl}carbamate

: tert-butyl N-{16-azido-9-[3-(p-methoxyphenyl)prop-2-enoyl]-13-(2,2,2-trichloro-tert-butoxycarbonyl)-5-(2-(trimethylsilyl)ethylsulfonyl)-5,9,13-triazahexadec-1-yl}carbamate

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / diisopropylethylamine; sodium iodide / toluene / 72 h / 100 °C

2: 75 percent / N,N'-dimethylbarbituric acid / tetrakis(triphenylphosphine)palladium / CH₂Cl₂ / 7 h / 35 °C

3: 70 percent / Et₃N / ethyl acetate / -10 - 20 °C

With 1,3-dimethylbarbituric acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; ethyl acetate; toluene; 1: Alkylation / 2: deallylation / 3: Acylation;
DOI:10.1021/jo980689e