N-[(1S)-1-methoxycarbonylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide

Base Information

• Chemical Name: N-[(1S)-1-methoxycarbonylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide
• CAS No.: 942509-55-9
• Molecular Formula: C₂₂H₂₅NO₄S
• Molecular Weight: 399.511

Synonyms:N-[(1S)-1-methoxycarbonylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide

Chemical Property of N-[(1S)-1-methoxycarbonylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide

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Technology Process of N-[(1S)-1-methoxycarbonylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide

There total 2 articles about N-[(1S)-1-methoxycarbonylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide 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: 74.0%

methyl (2S)-2-[(2,4,6-trimethylphenylsulfonyl)amino]propanoate (59724-80-0) + 1-bromo-3-phenylprop-2-yne (1794-48-5) → N-[(1S)-1-methoxycarbonylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide (942509-55-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jo0700528

Reference yield:

2-mesitylenesulphonyl chloride (773-64-8) → N-[(1S)-1-methoxycarbonylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide (942509-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 46 percent / Et₃N / dimethylformamide / 2.5 h / 20 °C

2: 74 percent / NaH / dimethylformamide / 2 h / 20 °C

With sodium hydride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jo0700528

Reference yield: 80.0%

N-[(1S)-1-methoxycarbonylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide (942509-55-9) → N-[(1S)-2-hydroxy-1-methylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide (942509-56-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1021/jo0700528

upstream raw materials:

methyl (2S)-2-[(2,4,6-trimethylphenylsulfonyl)amino]propanoate

1-bromo-3-phenylprop-2-yne

2-mesitylenesulphonyl chloride

Downstream raw materials:

N-[(1S)-2-hydroxy-1-methylethyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide

C₂₁H₂₃NO₃S

N-[(1S,Z)-3-bromo-3-methoxycarbonyl-1-methylprop-2-enyl]-2,4,6-trimethyl-N-[3-phenylprop-2-ynyl]phenylsulfonamide

N-[(1S,Z)-3-bromo-4-hydroxy-1-methylbut-2-enyl]-2,4,6-trimethyl-N-(3-phenylprop-2-ynyl)phenylsulfonamide

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