p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid

Base Information

• Chemical Name: p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid
• CAS No.: 1312311-21-9
• Molecular Formula: C₁₈H₂₁BN₂O₅S
• Molecular Weight: 388.252

Synonyms:

Chemical Property of p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid

Chemical Property:

Purity/Quality:

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Technology Process of p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid

There total 4 articles about p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid 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:

p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid pinacol ester (1312311-20-8) → p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid (1312311-21-9)

Guidance literature:

With sodium periodate; hydrochloric acid; In tetrahydrofuran; water; (N2); stirring of Me4C2BO2C6H4NHCOC4H7NTs and sodium periodate (3 equiv.) in 4:1 mixt. of THF and H2O for 1 h, addn. of aq. HCl (0.7 equiv.) to suspn., stirring at ambient temp. for 6 h; diluting with H2O and extn. with EtOAc, washing of combined org. layer with H2O ad brine, drying over anhyd. Na2SO4, decanting, evapn. of solvent;

DOI:10.1021/om2003078

Reference yield:

D-Prolin (344-25-2,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid (1312311-21-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 16 h / 20 °C

2.1: triethylamine / dichloromethane / 1 h / 0 °C

3.1: sodium periodate / tetrahydrofuran; water / 1 h

3.2: 6 h / 20 °C

With sodium periodate; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/om2003078

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid (1312311-21-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 16 h / 20 °C

2.1: triethylamine / dichloromethane / 1 h / 0 °C

3.1: sodium periodate / tetrahydrofuran; water / 1 h

3.2: 6 h / 20 °C

With sodium periodate; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/om2003078

upstream raw materials:

p-(N-p-toluenesulfonylpyrolinamido)phenyl boronic acid pinacol ester

(R)-N-tosylproline

p-toluenesulfonyl chloride

D-Prolin

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