tert-butyl (Z)-4-<(benzyoxycarbonyl)amino>-2-(fluoromethyl)-2-butenoate

Base Information

• Chemical Name: tert-butyl (Z)-4-<(benzyoxycarbonyl)amino>-2-(fluoromethyl)-2-butenoate
• CAS No.: 100702-83-8
• Molecular Formula: C₁₇H₂₂FNO₄
• Molecular Weight: 323.364
• Mol file: 100702-83-8.mol

Synonyms:tert-butyl (Z)-4-<(benzyoxycarbonyl)amino>-2-(fluoromethyl)-2-butenoate

Chemical Property of tert-butyl (Z)-4-<(benzyoxycarbonyl)amino>-2-(fluoromethyl)-2-butenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (Z)-4-<(benzyoxycarbonyl)amino>-2-(fluoromethyl)-2-butenoate

There total 4 articles about tert-butyl (Z)-4-<(benzyoxycarbonyl)amino>-2-(fluoromethyl)-2-butenoate 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: 55.0%

tert-butyl (E)-4-<(benzyoxycarbonyl)amino>-2-(hydroxymethyl)-2-butenoate (100702-81-6) → tert-butyl (Z)-4-<(benzyoxycarbonyl)amino>-2-(fluoromethyl)-2-butenoate (100702-83-8)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; 1.) -78 deg C, 1 h, 2.) RT, 1 h;

DOI:10.1021/jm00155a029

Reference yield:

4-(((benzyloxy)carbonyl)amino)butyric acid tert-butyl ester (5105-79-3) → tert-butyl (Z)-4-<(benzyoxycarbonyl)amino>-2-(fluoromethyl)-2-butenoate (100702-83-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) diisopropylamine, n-bytyllithium / 1.) THF, hexane, N,N,N',N'-tetramethylethylenediamine (TMEDA), -78 deg C, 30 min, 2.) THF, hexane, N,N,N',N'-tetramethylethylenediamine (TMEDA), -78 deg C, 30 min

2: 1.) diisopropylamine, n-butyllithium / 1.) THF, N,N,N',N'-tetramethylethylenediamine (TMEDA), hexane, -78 deg C, 10 min, 2.) THF, N,N,N',N'-tetramethylethylenediamine (TMEDA), hexane

3: 1.) m-chloroperoxybenzoic acid, 2.) diisopropylamine / 1.) dichloromethane, -10 deg C, 1 h, 2.) dichloromethane, CCl₄, reflux, 5 min

4: 55 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) RT, 1 h

With n-butyllithium; diethylamino-sulfur trifluoride; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jm00155a029

Reference yield:

tert-butyl 4-<(benzyoxycarbonyl)amino>-2-(phenylseleno)butanoate (100702-79-2) → tert-butyl (Z)-4-<(benzyoxycarbonyl)amino>-2-(fluoromethyl)-2-butenoate (100702-83-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) diisopropylamine, n-butyllithium / 1.) THF, N,N,N',N'-tetramethylethylenediamine (TMEDA), hexane, -78 deg C, 10 min, 2.) THF, N,N,N',N'-tetramethylethylenediamine (TMEDA), hexane

2: 1.) m-chloroperoxybenzoic acid, 2.) diisopropylamine / 1.) dichloromethane, -10 deg C, 1 h, 2.) dichloromethane, CCl₄, reflux, 5 min

3: 55 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) RT, 1 h

With n-butyllithium; diethylamino-sulfur trifluoride; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jm00155a029

upstream raw materials:

tert-butyl (E)-4-<(benzyoxycarbonyl)amino>-2-(hydroxymethyl)-2-butenoate

4-(((benzyloxy)carbonyl)amino)butyric acid tert-butyl ester

tert-butyl 4-<(benzyoxycarbonyl)amino>-2-(phenylseleno)butanoate

tert-butyl 4-<(benzyoxycarbonyl)amino>-2-(hydroxymethyl)-2-(phenylseleno)butanoate