(+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-ethylprop-1-yl]-p-tolylsulfinamide

Base Information

• Chemical Name: (+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-ethylprop-1-yl]-p-tolylsulfinamide
• CAS No.: 467471-51-8
• Molecular Formula: C₂₅H₄₀N₂O₂SSi
• Molecular Weight: 460.756

Synonyms:(+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-ethylprop-1-yl]-p-tolylsulfinamide

Chemical Property of (+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-ethylprop-1-yl]-p-tolylsulfinamide

Chemical Property:

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Technology Process of (+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-ethylprop-1-yl]-p-tolylsulfinamide

There total 1 articles about (+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-ethylprop-1-yl]-p-tolylsulfinamide 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: 88.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (+)-(2S,3R,SS)-2-(benzylamino)-3-(p-tolylsulfinylamino)pentan-1-ol (467471-29-0) → (+)-(1R,2S,SS)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-ethylprop-1-yl]-p-tolylsulfinamide (467471-51-8)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jo052077h

Reference yield: 82.0%

chloroacetyl chloride (79-04-9) + (+)-(1R,2S,SS)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-ethylprop-1-yl]-p-tolylsulfinamide (467471-51-8) → (+)-N-benzyl-N-[(1S,2R,SS)-1-(t-butyldimethylsilyloxymethyl)-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide (467471-53-0)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; at 0 - 20 ℃; for 2h;

DOI:10.1055/s-2002-25336

Reference yield:

(+)-(1R,2S,SS)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-ethylprop-1-yl]-p-tolylsulfinamide (467471-51-8) → (5R,6S)-1-benzyl-6-(tert-butyldimethylsilyloxymethyl)-5-ethyl-1,2,5,6-tetrahydropyrazin-2-one

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / aq. NaHCO₃ / ethyl acetate / 0 - 20 °C

2: 92 percent / Cs₂CO₃ / dimethylformamide / 2 h / 65 °C

3: 83 percent / NaH / tetrahydrofuran / 1 h / Heating

With sodium hydride; sodium hydrogencarbonate; caesium carbonate; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo052077h

upstream raw materials:

tert-butyldimethylsilyl chloride

(+)-(2S,3R,S_S)-2-(benzylamino)-3-(p-tolylsulfinylamino)pentan-1-ol

Downstream raw materials:

(+)-N-benzyl-N-[(1S,2R,S_S)-1-(t-butyldimethylsilyloxymethyl)-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide

(+)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-ethyl-4-(p-tolylsulfinyl)piperazin-2-one

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