N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide

Base Information

• Chemical Name: N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide
• CAS No.: 212195-38-5
• Molecular Formula: C₂₁H₂₇NO₄S
• Molecular Weight: 389.516

Synonyms:N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide

Chemical Property of N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide

There total 15 articles about N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide 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: 87.0%

N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]ethanesulfonamide (518358-59-3) + methyl iodide (74-88-4) → N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide (212195-38-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h;

DOI:10.1002/1522-2675(200211)85:11<3657::AID-HLCA3657>3.0.CO;2-A

Reference yield:

methyl rac-2-amino-3-(biphenyl-4-yl)-3-hydroxypropanoate (101293-94-1) → N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide (212195-38-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1H-imidazole / acetonitrile / 3 h / 40 °C

2.1: 69 g / iPr₂NEt / toluene / 96 h / Heating

3.1: DIBAL-H / CH₂Cl₂ / 8 h / 0 °C

4.1: 34.5 g / Bu₄NF / tetrahydrofuran / 2 h

5.1: 84 percent / camphorsulfonic acid / toluene / 96 h / Heating

6.1: 99 percent / [RhCl(PPh₃)3] / acetonitrile; H₂O / 1.5 h / Heating

7.1: L-(+)-tartaric acid / ethanol / Heating

7.2: aq. NaOH

8.1: 81 percent / Et₃N / CH₂Cl₂ / 20 °C

9.1: 87 percent / BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; L-Tartaric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; tris(triphenylphosphine)rhodium(I) chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1002/1522-2675(200211)85:11<3657::AID-HLCA3657>3.0.CO;2-A

Reference yield:

4-Phenylbenzaldehyde (3218-36-8) → N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide (212195-38-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: aq. NaOH / ethanol / 4.5 h

1.2: SOCl₂ / 5 h / Heating

2.1: 1H-imidazole / acetonitrile / 3 h / 40 °C

3.1: 69 g / iPr₂NEt / toluene / 96 h / Heating

4.1: DIBAL-H / CH₂Cl₂ / 8 h / 0 °C

5.1: 34.5 g / Bu₄NF / tetrahydrofuran / 2 h

6.1: 84 percent / camphorsulfonic acid / toluene / 96 h / Heating

7.1: 99 percent / [RhCl(PPh₃)3] / acetonitrile; H₂O / 1.5 h / Heating

8.1: L-(+)-tartaric acid / ethanol / Heating

8.2: aq. NaOH

9.1: 81 percent / Et₃N / CH₂Cl₂ / 20 °C

10.1: 87 percent / BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

With 1H-imidazole; sodium hydroxide; n-butyllithium; L-Tartaric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; tris(triphenylphosphine)rhodium(I) chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1002/1522-2675(200211)85:11<3657::AID-HLCA3657>3.0.CO;2-A

upstream raw materials:

N-[(4S,5S)-4-(biphenyl-4-yl)-2,2-dimethyl-1,3-dioxan-5-yl]ethanesulfonamide

methyl iodide

methyl rac-2-amino-3-(biphenyl-4-yl)-3-hydroxypropanoate

4-Phenylbenzaldehyde

Downstream raw materials:

(R)-1-Phenyl-propane-2-sulfonic acid ((4S,5S)-4-biphenyl-4-yl-2,2-dimethyl-[1,3]dioxan-5-yl)-methyl-amide

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