Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))-

Base Information

• Chemical Name: Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))-
• CAS No.: 19934-71-5
• Molecular Formula: C12H15 Cl2 N O5 S
• Molecular Weight: 356.22
• Mol file: 19934-71-5.mol

Synonyms:Acetamide,2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-,[S-(R*,R*)]-; Acetamide, 2,2-dichloro-N-[b-hydroxy-a-(hydroxymethyl)-p-(methylsulfonyl)phenethyl]-, L-threo- (8CI);Thiamphenicol epimer; Win 5063-3

Chemical Property of Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))-

Chemical Property:

• Vapor Pressure: 2.5E-20mmHg at 25°C
• Boiling Point: 695.9°Cat760mmHg
• Flash Point: 374.7°C
• PSA: 112.08000
• Density: 1.491g/cm³
• LogP: 1.87600

Purity/Quality:

98% ^*data from raw suppliers

ent-Thiamphenicol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The enatiomeric analogue of the antimicrobial agent Thiamphenicol (T344160).

Technology Process of Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))-

There total 28 articles about Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))- 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: 72.0%

ethyl 2-(2,2-dichloroacetamido)-3-hydroxy-3-[4-(methylsulfonyl)phenyl]propanoate → 2,2-dichloro-N-{1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]propan-2-yl}acetamide (19934-71-5,90-91-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;

DOI:10.1002/ejoc.201500661

Reference yield:

(1RS,2RS)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol (4302-89-0,6631-50-1,13185-24-5,14052-59-6,27348-37-4,27348-49-8,27348-50-1,71830-03-0) → (+/-)-Thiamphenicol (847-25-6,7780-07-6,15318-45-3,19934-71-5,21079-44-7,27348-38-5,27348-52-3,90-91-5)

Guidance literature:

With peracetic acid;

DOI:10.1021/ja01141a074

Reference yield:

→ (+/-)-Thiamphenicol (847-25-6,7780-07-6,15318-45-3,19934-71-5,21079-44-7,27348-38-5,27348-52-3,90-91-5)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol;

DOI:10.1021/ja01113a057

upstream raw materials:

pentachloroacetone

(1S,2S)-2-amino-1-(4-(methylsulfonyl)phenyl)propane-1,3-diol

(1S,2S)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol

methyl iodide

Downstream raw materials:

(1S,2S)-2-amino-1-(4-(methylsulfonyl)phenyl)propane-1,3-diol

(1RS,2RS)-2-amino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol

Refernces

• 1、 McCombie, S. W.,Nagabhushan, T. L.. "CYCLOFUNCTIONALISATION REACTIONS OF EPOXYALCOHOL DERIVATIVES. 3. CYCLISATION-ACYL MIGRATION OF N-BENZOYLCARBAMATES TO STEREODEFINED OXAZOLIDINONES. A NEW, DIASTEREOSPECIFIC ROUTE TO THIAMPHENICOL.". . p. 5395 - 5398. Retrieved 2007/10/02.