(2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate

Base Information

• Chemical Name: (2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate
• CAS No.: 1255203-09-8
• Molecular Formula: C₁₆H₂₂FNO₅
• Molecular Weight: 327.353
• Mol file: 1255203-09-8.mol

Synonyms:(2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate

Chemical Property of (2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate

There total 8 articles about (2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate 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: 89.0%

ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-oxopropanoate (334705-19-0) → (2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate (1255203-09-8)

Guidance literature:

With dichloro(benzene)ruthenium(II) dimer; triethylammonium formate; (1S,2S)-2-(benzylamino)-1,2-diphenylethanol; In isopropyl alcohol; at 20 ℃; for 168h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ol102323k

Reference yield:

ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-oxopropanoate (334705-19-0) → (2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate (1255203-09-8) + ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate

Guidance literature:

With dichloro(benzene)ruthenium(II) dimer; sodium formate; tetra-(n-butyl)ammonium iodide; triethylamine; (1S,2S)-2-(benzylamino)-1,2-diphenylethanol; In dichloromethane; water; at 0 - 20 ℃; pH=7; optical yield given as %ee; enantioselective reaction; Sonication;

DOI:10.1002/chem.201103739

Reference yield:

diethyl tert-butoxycarbonylaminomalonate (102831-44-7) → (2S,3S)-ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-hydroxypropanoate (1255203-09-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide

2.1: triethylamine; magnesium chloride / tetrahydrofuran / 2 h / 0 °C

2.2: 0 - 20 °C

3.1: dichloro(benzene)ruthenium(II) dimer; formic acid/triethylamine complex 5:2; (1S,2S)-2-(benzylamino)-1,2-diphenylethanol / isopropyl alcohol / 168 h / 20 °C

With dichloro(benzene)ruthenium(II) dimer; formic acid/triethylamine complex 5:2; triethylamine; sodium hydroxide; magnesium chloride; (1S,2S)-2-(benzylamino)-1,2-diphenylethanol; In tetrahydrofuran; isopropyl alcohol;

DOI:10.1002/chem.201103739

upstream raw materials:

ethyl 2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)-3-oxopropanoate

4-Fluorobenzoic acid

4-fluorobenzoyl chloride

2-{[(tert-butoxy)carbonyl]amino}-3-ethoxy-3-oxopropanoic acid