(S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine

Base Information

• Chemical Name: (S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine
• CAS No.: 1425458-21-4
• Molecular Formula: C₃₀H₃₄ClN₃O₂S
• Molecular Weight: 536.138

Synonyms:(S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine

Chemical Property of (S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine

Chemical Property:

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Technology Process of (S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine

There total 2 articles about (S_S,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine 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: 57.0%

(SS)-α-chloro-N-p-toluenesulfinyl isobutyraldimine (1365547-75-6) + N-(diphenylmethylene)-2-oxo-2-(pyrrolidin-1-yl)ethanamine (147032-42-6) → (SS,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine (1425458-21-4)

Guidance literature:

N-(diphenylmethylene)-2-oxo-2-(pyrrolidin-1-yl)ethanamine; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

(S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine; In tetrahydrofuran; at -78 ℃; for 0.25h; diastereoselective reaction; Inert atmosphere;

DOI:10.3762/bjoc.8.239

Reference yield:

(S)-p-toluenesulfinimide (188447-91-8) → (SS,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine (1425458-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium(IV) tetraethanolate / dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 0.25 h / -78 °C / Inert atmosphere

With titanium(IV) tetraethanolate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.3762/bjoc.8.239

Reference yield: 70.0%

(SS,2S,3S)-N-[4-chloro-2-(diphenylmethyleneamino)-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine (1425458-21-4) → (SS,2S,3S)-N-[2-amino-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoyl]pyrrolidine

Guidance literature:

With trifluoroacetic acid; In water; acetone; at 20 ℃; for 0.25h;

DOI:10.3762/bjoc.8.239

upstream raw materials:

(S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine

N-(diphenylmethylene)-2-oxo-2-(pyrrolidin-1-yl)ethanamine

(S)-p-toluenesulfinimide

Downstream raw materials:

(S_S,2S,2'S)-N-{2-(diphenylmethyleneamino)-2-[3,3-dimethyl-1-(p-toluenesulfinyl)aziridin-2-yl]acetyl}pyrrolidine

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