(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester

Base Information

• Chemical Name: (2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester
• CAS No.: 159721-18-3
• Molecular Formula: C₁₇H₁₈N₂O₆S
• Molecular Weight: 378.406
• Mol file: 159721-18-3.mol

Synonyms:(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester

Chemical Property of (2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester

There total 1 articles about (2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester 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:

benzyl bromide (100-39-0) + N-(2-nitrobenzenesulfonyl)-(S)-alanine methyl ester (215056-53-4) → (2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester (159721-18-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/jo0606002

Reference yield: 88.0%

(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester (159721-18-3) + vinylmagnesium chloride (3536-96-7) → (3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]pent-1-en-3-ol (898831-79-3)

Guidance literature:

(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester; With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;

vinylmagnesium chloride; With lithium chloride; zinc(II) chloride; In tetrahydrofuran; at 0 ℃; for 0.5h;

In tetrahydrofuran; dichloromethane; toluene; at 0 ℃; for 2h;

DOI:10.1021/jo0606002

Reference yield:

(2S)-2-[benzyl(2-nitrobenzenesulfonyl)amino]propionic acid methyl ester (159721-18-3) → (5S,6S)-1-Benzyl-5-hydroxy-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

Guidance literature:

Multi-step reaction with 12 steps

1.1: DIBAL-H / toluene; CH₂Cl₂ / 0.5 h / -78 °C

1.2: ZnCl₂; LiCl / tetrahydrofuran / 0.5 h / 0 °C

1.3: 88 percent / CH₂Cl₂; toluene; tetrahydrofuran / 2 h / 0 °C

2.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

3.1: O₃ / ethyl acetate / 1.33 h / -78 °C

3.2: Me₂S / ethyl acetate / -78 - 0 °C

4.1: 2-methyl-2-butene; NaH₂PO₄*2H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 15 h / 20 °C

5.1: SOCl₂ / 1 h / Heating

6.1: 87.1 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

7.1: LiOH*2H₂O; mercaptoacetic acid / dimethylformamide / 4 h

8.1: (i-Pr)2NEt / CH₂Cl₂ / 20 °C

9.1: NaOEt / ethanol / 0 - 20 °C

9.2: H₂O / acetonitrile / Heating

10.1: Et₃N / CH₂Cl₂ / 20 °C

11.1: (Me₃Sn)2; LiCl / PdCl₂[P(o-tolyl)3]2 / tetrahydrofuran

11.2: iodine / CH₂Cl₂ / 20 °C

12.1: TBAF / tetrahydrofuran / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; sodium ethanolate; hexamethyldistannane; diisobutylaluminium hydride; ozone; mercaptoacetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo0606002

upstream raw materials:

benzyl bromide

N-(2-nitrobenzenesulfonyl)-(S)-alanine methyl ester

Downstream raw materials:

(3R,4S)-4-[benzyl(2-nitrobenzenesulfonyl)amino]pent-1-en-3-ol

(2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-hydroxybutyric acid ethyl ester

(5S,6S)-1-benzyl-5-diphenylphosphoryloxy-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

(5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one