(S_s,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate

Base Information

• Chemical Name: (S_s,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate
• CAS No.: 1609490-94-9
• Molecular Formula: C₂₀H₃₀ClNO₆S
• Molecular Weight: 447.98

Synonyms:(S_s,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate

Chemical Property of (S_s,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate

Chemical Property:

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Technology Process of (S_s,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate

There total 2 articles about (S_s,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 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%

(SS)-α-chloro-N-p-toluenesulfinyl isobutyraldimine (1365547-75-6) + ethyl 2-(tert-butoxycarbonyloxy)acetate (1609490-80-3) → (Ss,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate (1609490-94-9) + (Ss)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate

Guidance literature:

ethyl 2-(tert-butoxycarbonyloxy)acetate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

(S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine; In tetrahydrofuran; at -78 ℃; for 5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/c4ob00243a

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (Ss,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate (1609490-94-9) + (Ss)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap / acetonitrile / 18 h / 20 °C

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

2.2: 5 h / -78 °C / Inert atmosphere

With dmap; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile; 2.2: |Mannich Aminomethylation;

DOI:10.1039/c4ob00243a

Reference yield: 82.0%

(Ss,2S,3S)-ethyl 2-(tert-butoxycarbonyloxy)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate (1609490-94-9) → (Ss,2S,2′R)-ethyl 2-(tert-butoxycarbonyloxy)-2-(3,3-dimethyl-1-p-toluenesulfinylaziridin-2-yl)acetate

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 24h; Reflux;

DOI:10.1039/c4ob00243a

upstream raw materials:

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

ethyl 2-(tert-butoxycarbonyloxy)acetate

di-tert-butyl dicarbonate

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