C₁₆H₂₂⁽²⁾HBClNO₄

Base Information

• Chemical Name: C₁₆H₂₂⁽²⁾HBClNO₄
• CAS No.: 1269416-95-6
• Molecular Formula: C₁₆H₂₃BClNO₄
• Molecular Weight: 340.619
• Mol file: 1269416-95-6.mol

Synonyms:C₁₆H₂₂⁽²⁾HBClNO₄

Chemical Property of C₁₆H₂₂⁽²⁾HBClNO₄

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of C₁₆H₂₂⁽²⁾HBClNO₄

There total 1 articles about C₁₆H₂₂⁽²⁾HBClNO₄ 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:

2-[(SS,2R)-2-chloro-2-deutero-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane (1269417-04-0) + 2-chloro-5-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (444120-94-9) → C16H22(2)HBClNO4 (1269416-95-6) + (R)-1-methyl-4-(phenylsulfinyl)benzene (16491-20-6)

Guidance literature:

With phenyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol103170y

Reference yield: 23.0%

2-[(SS,2R)-2-chloro-2-deutero-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane (1269417-04-0) + C16H22(2)HBClNO4 (1269416-95-6) → C10H11(2)HClNO2 (1269416-97-8) + C10H11(2)HClNO3 (1269417-10-8) + C15H18(2)H2ClNO5 (1269416-96-7) + (R)-1-methyl-4-(phenylsulfinyl)benzene (16491-20-6)

Guidance literature:

2-[(SS,2R)-2-chloro-2-deutero-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane; C₁₆H₂₂⁽²⁾HBClNO₄; With phenyllithium; In tetrahydrofuran; dibutyl ether; at -78 - 20 ℃; for 3h; Inert atmosphere;

With dihydrogen peroxide; potassium hydroxide; In tetrahydrofuran; dibutyl ether; water; at 20 ℃; for 1.5h; optical yield given as %de;

DOI:10.1021/ol103170y

Reference yield:

C16H22(2)HBClNO4 (1269416-95-6) → C13H10(2)H2ClF3N2O (1269417-00-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: phenyllithium / tetrahydrofuran; dibutyl ether / 3 h / -78 - 20 °C / Inert atmosphere

1.2: 1.5 h / 20 °C

2.1: triethylamine / dichloromethane / 0.58 h / 0 °C / Inert atmosphere

3.1: sodium azide / N,N-dimethyl-formamide / 6 h / Inert atmosphere; Heating

4.1: toluene-4-sulfonic acid / 17.5 h / Reflux

5.1: trifluoroacetic acid / chloroform; water / 2 h / 20 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / 0 °C / Inert atmosphere

6.2: 2.25 h / -10 - 20 °C / Inert atmosphere; Reflux

6.3: 17.5 h / 20 °C

7.1: Grubbs catalyst first generation / dichloromethane / 0.75 h / Inert atmosphere; Reflux

With Grubbs catalyst first generation; n-butyllithium; sodium azide; toluene-4-sulfonic acid; phenyllithium; triethylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform; dibutyl ether; water; N,N-dimethyl-formamide; 6.1: Wittig-Staudinger reaction / 6.2: Wittig-Staudinger reaction;

DOI:10.1021/ol103170y

upstream raw materials:

2-[(SS,2R)-2-chloro-2-deutero-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane

2-chloro-5-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Downstream raw materials:

C₁₀H₁₁⁽²⁾HClNO₂

C₁₀H₁₁⁽²⁾HClNO₃

C₁₅H₁₈⁽²⁾H₂ClNO₅

(R)-1-methyl-4-(phenylsulfinyl)benzene

Refernces