(+)-(1R,S_S)-p-toluenesulfinic acid [1-(4-benzyl-5,6-dioxomorpholin-3-(S)-yl)-propyl]amide

Base Information

• Chemical Name: (+)-(1R,S_S)-p-toluenesulfinic acid [1-(4-benzyl-5,6-dioxomorpholin-3-(S)-yl)-propyl]amide
• CAS No.: 467471-39-2
• Molecular Formula: C₂₁H₂₄N₂O₄S
• Molecular Weight: 400.499

Synonyms:(+)-(1R,S_S)-p-toluenesulfinic acid [1-(4-benzyl-5,6-dioxomorpholin-3-(S)-yl)-propyl]amide

Chemical Property of (+)-(1R,S_S)-p-toluenesulfinic acid [1-(4-benzyl-5,6-dioxomorpholin-3-(S)-yl)-propyl]amide

Chemical Property:

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Technology Process of (+)-(1R,S_S)-p-toluenesulfinic acid [1-(4-benzyl-5,6-dioxomorpholin-3-(S)-yl)-propyl]amide

There total 1 articles about (+)-(1R,S_S)-p-toluenesulfinic acid [1-(4-benzyl-5,6-dioxomorpholin-3-(S)-yl)-propyl]amide 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: 79.0%

oxalic acid diethyl ester (95-92-1) + (+)-(2S,3R,SS)-2-(benzylamino)-3-(p-tolylsulfinylamino)pentan-1-ol (467471-29-0) → (+)-(5R,6S)-1-benzyl-5-ethyl-6-hydroxymethylpiperazine-2,3-dione (467471-34-7) + (+)-(1R,SS)-p-toluenesulfinic acid [1-(4-benzyl-5,6-dioxomorpholin-3-(S)-yl)-propyl]amide (467471-39-2)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; at 20 ℃;

DOI:10.1055/s-2002-25336

Reference yield:

(+)-(1R,SS)-p-toluenesulfinic acid [1-(4-benzyl-5,6-dioxomorpholin-3-(S)-yl)-propyl]amide (467471-39-2) → (+)-(5R,6S)-1-benzyl-5-ethyl-6-hydroxymethylpiperazine-2,3-dione (467471-34-7)

Guidance literature:

With sodium methylate; In methanol; for 1h;

DOI:10.1055/s-2002-25336

Reference yield:

(+)-(1R,SS)-p-toluenesulfinic acid [1-(4-benzyl-5,6-dioxomorpholin-3-(S)-yl)-propyl]amide (467471-39-2) → (-)-(2S,3R)-1-benzyl-3-ethyl-2-hydroxymethylpiperazine (467471-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methoxide / methanol / 1 h / 20 °C

2: 75 percent / borane dimethyl sulfide complex / tetrahydrofuran / 7 h / Heating

With dimethylsulfide borane complex; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1021/jo052077h

upstream raw materials:

oxalic acid diethyl ester

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

Downstream raw materials:

(+)-(5R,6S)-1-benzyl-5-ethyl-6-hydroxymethylpiperazine-2,3-dione

(-)-(2S,3R)-1-benzyl-3-ethyl-2-hydroxymethylpiperazine

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