(2S,3R)-1-chloroacetylamino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol

Base Information

• Chemical Name: (2S,3R)-1-chloroacetylamino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol
• CAS No.: 1045859-00-4
• Molecular Formula: C₁₉H₂₁BrClNO₄
• Molecular Weight: 442.737
• Mol file: 1045859-00-4.mol

Synonyms:(2S,3R)-1-chloroacetylamino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol

Chemical Property of (2S,3R)-1-chloroacetylamino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1-chloroacetylamino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol

There total 7 articles about (2S,3R)-1-chloroacetylamino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol 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: 83.0%

(2S,3R)-1-amino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol (1028547-05-8) + chloroacetyl chloride (79-04-9) → (2S,3R)-1-chloroacetylamino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol (1045859-00-4)

Guidance literature:

With triethylamine;

DOI:10.1002/jlcr.1242

Reference yield:

ethyl (E)-3-(4-bromophenyl)-2-propenoate (24393-53-1,136265-11-7,15795-20-7) → (2S,3R)-1-chloroacetylamino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol (1045859-00-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 72 percent / DIBAL-H

2: 74 percent / t-BuOOH; (+)-DIPT / Ti(O-iPr)4

3: 65 percent / NEt₃; DMAP

4: 49 percent / ammonium hydroxide

5: 83 percent / NEt₃

With tert.-butylhydroperoxide; dmap; ammonium hydroxide; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; triethylamine; titanium(IV) isopropylate; 2: Sharpless asymmetric epoxidation;

DOI:10.1002/jlcr.1242

Reference yield:

(2E)-3-(4-bromophenyl)prop-2-en-1-ol (105515-33-1) → (2S,3R)-1-chloroacetylamino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol (1045859-00-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / t-BuOOH; (+)-DIPT / Ti(O-iPr)4

2: 65 percent / NEt₃; DMAP

3: 49 percent / ammonium hydroxide

4: 83 percent / NEt₃

With tert.-butylhydroperoxide; dmap; ammonium hydroxide; L-(+)-diisopropyl tartrate; triethylamine; titanium(IV) isopropylate; 1: Sharpless asymmetric epoxidation;

DOI:10.1002/jlcr.1242

upstream raw materials:

(2S,3R)-1-amino-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propan-2-ol

chloroacetyl chloride

(2S,3R)-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)propane-1,2-diol

(2S,3R)-3-(4-bromophenyl)-3-(2-ethoxyphenoxy)-1-(toluenesulfonyloxy)propan-2-ol

Downstream raw materials:

(2S,3R)-2-[(4-bromophenyl)-(2-ethoxyphenoxy)methyl]morpholin-5-one

(2S,3R)-2-[(4-bromophenyl)-(2-ethoxyphenoxy)methyl]morpholine

(2S,3R)-2-[(4-bromophenyl)-(2-ethoxyphenoxy)methyl]-N-tert-butoxycarbonylmorpholine

(2S,3R)-2-[(4-iodophenyl)-(2-ethoxyphenoxy)methyl]-N-tert-butoxycarbonylmorpholine