(+)-N-benzyl-N-[(1S,2R,S_S)-1-(hydroxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide

Base Information

• Chemical Name: (+)-N-benzyl-N-[(1S,2R,S_S)-1-(hydroxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide
• CAS No.: 878556-93-5
• Molecular Formula: C₂₉H₂₉ClN₂O₃S
• Molecular Weight: 521.08

Synonyms:(+)-N-benzyl-N-[(1S,2R,S_S)-1-(hydroxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide

Chemical Property of (+)-N-benzyl-N-[(1S,2R,S_S)-1-(hydroxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide

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Technology Process of (+)-N-benzyl-N-[(1S,2R,S_S)-1-(hydroxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide

There total 2 articles about (+)-N-benzyl-N-[(1S,2R,S_S)-1-(hydroxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-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: 52.0%

(-)-(2S,3R,SS)-2-(benzylamino)-3-(1-naphthyl)-3-(p-tolylsulfinylamino)propan-1-ol (878556-85-5) + chloroacetyl chloride (79-04-9) → (+)-N-benzyl-N-[(1S,2R,SS)-1-(hydroxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide (878556-93-5)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/jo052077h

Reference yield:

methyl [(2S,4S,5R,SS)-5-(1-naphthyl)-2-phenyl-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate (596823-41-5) → (+)-N-benzyl-N-[(1S,2R,SS)-1-(hydroxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide (878556-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / LiAlH₄ / diethyl ether / 4 h

2: 52 percent / aq. NaHCO₃ / ethyl acetate / 1.5 h / 0 - 20 °C

With lithium aluminium tetrahydride; sodium hydrogencarbonate; In diethyl ether; ethyl acetate;

DOI:10.1021/jo052077h

Reference yield: 31.0%

(+)-N-benzyl-N-[(1S,2R,SS)-1-(hydroxymethyl)-2-(1-naphthyl)-2-(p-tolylsulfinylamino)ethyl]-2-chloroacetamide (878556-93-5) → (-)-(5R,6S,SS)-1-benzyl-6-hydroxymethyl-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 65 ℃; for 4h;

DOI:10.1021/jo052077h

upstream raw materials:

(-)-(2S,3R,S_S)-2-(benzylamino)-3-(1-naphthyl)-3-(p-tolylsulfinylamino)propan-1-ol

chloroacetyl chloride

methyl [(2S,4S,5R,S_S)-5-(1-naphthyl)-2-phenyl-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate

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