(2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate

Base Information

• Chemical Name: (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate
• CAS No.: 1284258-89-4
• Molecular Formula: C₂₅H₂₅NO₄S
• Molecular Weight: 435.544
• Mol file: 1284258-89-4.mol

Synonyms:(2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate

Chemical Property of (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate

There total 2 articles about (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate 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: 67.0%

diazoacetic acid ethyl ester (623-73-4) + N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine (1284258-88-3) → (2R,3R)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate + (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate (1284258-89-4)

Guidance literature:

N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine; With (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; triphenylborane; In toluene; at 20 ℃; for 0.166667h; Molecular sieve; Inert atmosphere;

diazoacetic acid ethyl ester; In toluene; at -10 - 20 ℃; for 19h; optical yield given as %ee; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.052

Reference yield:

para-methanesulfonylbenzaldehyde (5398-77-6) → (2R,3R)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate + (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate (1284258-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ethanol / 3 h / Inert atmosphere; Reflux

2.1: (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; triphenylborane / toluene / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 19 h / -10 - 20 °C / Molecular sieve; Inert atmosphere

With (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; triphenylborane; In ethanol; toluene; 2.1: Wulff aziridination / 2.2: Wulff aziridination;

DOI:10.1016/j.tet.2011.09.052

Reference yield: 95.0%

(2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate (1284258-89-4) → ((2S,3S)-1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridin-2-yl)methanol (1284258-90-7)

Guidance literature:

(2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridine-2-carboxylate; With lithium borohydride; In tetrahydrofuran; at 50 ℃; Inert atmosphere;

With water; In tetrahydrofuran; at 20 ℃; for 1h; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.052

upstream raw materials:

diazoacetic acid ethyl ester

N-(4-(methylsulfonyl)benzylidene)diphenylmethanamine

para-methanesulfonylbenzaldehyde

Downstream raw materials:

((2S,3S)-1-benzhydryl-3-(4-(methylsulfonyl)phenyl)aziridin-2-yl)methanol

(1R,2S)-2-(benzhydrylamino)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propan-1-ol

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol

Florfenicol

Refernces