4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid

Base Information

• Chemical Name: 4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid
• CAS No.: 124688-44-4
• Molecular Formula: C₁₄H₁₄FNO₆
• Molecular Weight: 311.267
• Mol file: 124688-44-4.mol

Synonyms:

Chemical Property of 4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid

There total 2 articles about 4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid 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: 65.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-benzyloxycarbonyl-4-(R/S)-fluoro-D/L-glutamic acid (124688-42-2,124688-43-3) → 4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid (124688-44-4,124688-45-5)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 7h; Heating;

DOI:10.1021/jm00165a021

Reference yield:

D,L-erythro,threo-4-fluoroglutamic acid (2708-77-2,149117-03-3,91383-48-1,91383-47-0) → 4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid (124688-44-4,124688-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / NaHCO₃ / H₂O / 5 h

2: 65 percent / TsOH / benzene / 7 h / Heating

With sodium hydrogencarbonate; toluene-4-sulfonic acid; In water; benzene;

DOI:10.1021/jm00165a021

Reference yield: 50.0%

di-tert-butyl L-glutamate (16874-06-9) + 4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionic acid (124688-44-4,124688-45-5) → N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester (124688-46-6,124815-52-7,124815-53-8,124815-54-9)

Guidance literature:

With benzotriazol-1-ol; 2`,3`-dideoxycytidine; In dichloromethane; for 72h; Ambient temperature;

DOI:10.1021/jm00165a021

upstream raw materials:

formaldehyd

N-benzyloxycarbonyl-4-(R/S)-fluoro-D/L-glutamic acid

D,L-erythro,threo-4-fluoroglutamic acid

Downstream raw materials:

N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester

Refernces