(+)-N-benzyl-N-[(1S,2R,S_S)-1-(t-butyldimethylsilyloxymethyl)-3-methyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide

Base Information

• Chemical Name: (+)-N-benzyl-N-[(1S,2R,S_S)-1-(t-butyldimethylsilyloxymethyl)-3-methyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide
• CAS No.: 878556-91-3
• Molecular Formula: C₂₈H₄₃ClN₂O₃SSi
• Molecular Weight: 551.266

Synonyms:(+)-N-benzyl-N-[(1S,2R,S_S)-1-(t-butyldimethylsilyloxymethyl)-3-methyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide

Chemical Property of (+)-N-benzyl-N-[(1S,2R,S_S)-1-(t-butyldimethylsilyloxymethyl)-3-methyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide

Chemical Property:

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Technology Process of (+)-N-benzyl-N-[(1S,2R,S_S)-1-(t-butyldimethylsilyloxymethyl)-3-methyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide

There total 3 articles about (+)-N-benzyl-N-[(1S,2R,S_S)-1-(t-butyldimethylsilyloxymethyl)-3-methyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide 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: 75.0%

(+)-(1R,2S,SS)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(i-propyl)prop-1-yl]-p-tolylsulfinamide (878556-88-8) + chloroacetyl chloride (79-04-9) → (+)-N-benzyl-N-[(1S,2R,SS)-1-(t-butyldimethylsilyloxymethyl)-3-methyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide (878556-91-3)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; at 0 - 20 ℃; for 22h;

DOI:10.1021/jo052077h

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (+)-N-benzyl-N-[(1S,2R,SS)-1-(t-butyldimethylsilyloxymethyl)-3-methyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide (878556-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 75 percent / aq. NaHCO₃ / ethyl acetate / 22 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium hydrogencarbonate; In dichloromethane; ethyl acetate;

DOI:10.1021/jo052077h

Reference yield:

(+)-(2S,3R,SS)-2-(benzylamino)-4-methyl-3-(p-tolylsulfinylamino)pentan-1-ol (467471-31-4) → (+)-N-benzyl-N-[(1S,2R,SS)-1-(t-butyldimethylsilyloxymethyl)-3-methyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide (878556-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 75 percent / aq. NaHCO₃ / ethyl acetate / 22 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium hydrogencarbonate; In dichloromethane; ethyl acetate;

DOI:10.1021/jo052077h

upstream raw materials:

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

chloroacetyl chloride

tert-butyldimethylsilyl chloride

(+)-(2S,3R,S_S)-2-(benzylamino)-4-methyl-3-(p-tolylsulfinylamino)pentan-1-ol

Downstream raw materials:

(+)-(5R,6S)-1-benzyl-6-(t-butyldimethylsilyloxymethyl)-5-(i-propyl)-5,6-dihydro-1H-pyrazin-2-one

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

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