(S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide

Base Information

• Chemical Name: (S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide
• CAS No.: 507453-94-3
• Molecular Formula: C₁₈H₂₂N₂O₃S
• Molecular Weight: 346.45

Synonyms:(S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide

Chemical Property of (S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide

Chemical Property:

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Technology Process of (S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide

There total 3 articles about (S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide 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: 78.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (SS,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate (158009-86-0) → (SS,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide (507453-94-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 2h;

DOI:10.1021/ol034119z

Reference yield: 65.0%

N-Methoxy-N-methylacetamide (78191-00-1) + (S)-N-benzylidene-4-toluenesulfinamide (153277-49-7) → (SS,3S)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide + (SS,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide (507453-94-3)

Guidance literature:

N-Methoxy-N-methylacetamide; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 1h;

(S)-N-benzylidene-4-toluenesulfinamide; In tetrahydrofuran; at -78 ℃; for 2.5h;

With ammonium chloride; In tetrahydrofuran; water; at -78 - 20 ℃;

DOI:10.1021/jo801653c

Reference yield: 52.0%

N-Methoxy-N-methylacetamide (78191-00-1) + (S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) → (SS,3S)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide + (SS,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide (507453-94-3)

Guidance literature:

N-Methoxy-N-methylacetamide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

(S,E)-N-benzylidene-4-methylbenzenesulfinamide; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

DOI:10.1021/ol034119z

upstream raw materials:

N-Methoxy-N-methylacetamide

(S,E)-N-benzylidene-4-methylbenzenesulfinamide

N,O-dimethylhydroxylamine*hydrochloride

(S_S,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate

Downstream raw materials:

(S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-1-methyl-3-(phenyl)propan-1-one

(S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-1,3-di(phenyl)propan-1-one

(S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propionaldehyde

dimethyl (S_S,R)-(+)-2-oxo-4-(p-toluenesulfinylamino)-4-phenyl-butylphosphonate

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