tert-butyl 2-(benzhydrylideneamino)-4-fluoropent-4-enoate

Base Information

• Chemical Name: tert-butyl 2-(benzhydrylideneamino)-4-fluoropent-4-enoate
• CAS No.: 215716-69-1
• Molecular Formula: C₂₂H₂₄FNO₂
• Molecular Weight: 353.436
• Mol file: 215716-69-1.mol

Synonyms:tert-butyl 2-(benzhydrylideneamino)-4-fluoropent-4-enoate

Chemical Property of tert-butyl 2-(benzhydrylideneamino)-4-fluoropent-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 2-(benzhydrylideneamino)-4-fluoropent-4-enoate

There total 2 articles about tert-butyl 2-(benzhydrylideneamino)-4-fluoropent-4-enoate 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: 96.0%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + 2-fluoroallyl 4-methylbenzenesulfonate → tert-butyl 2-(benzhydrylideneamino)-4-fluoropent-4-enoate (215716-69-1)

Guidance literature:

N-(diphenylmethylene)glycine tert-butyl ester; With potassium carbonate; In dimethyl sulfoxide; for 0.5h; Schlenk technique; Inert atmosphere;

2-fluoroallyl 4-methylbenzenesulfonate; In dimethyl sulfoxide; for 4h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.jfluchem.2013.03.011

Reference yield: 95.0%

3-bromo-2-fluoroprop-1-ene (35386-83-5) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → tert-butyl 2-(benzhydrylideneamino)-4-fluoropent-4-enoate (215716-69-1)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.) -78 deg C, 1 h, 2.) -78 deg C, 2 h; -78 deg C to r.t., overnight;

DOI:10.1055/s-1998-2174

Reference yield:

tert-butyl 2-(benzhydrylideneamino)-4-fluoropent-4-enoate (215716-69-1) → tert-butyl 4-fluoro-2-(7-trityloxycarbamoylheptanoylamino)pent-4-enoate

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / methanol / 1 h / 20 °C

2.1: 4-methyl-morpholine / tetrahydrofuran / 0.17 h / 20 °C

2.2: 1.42 h / -10 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; In tetrahydrofuran; methanol;

DOI:10.1016/j.jfluchem.2013.03.011

upstream raw materials:

3-bromo-2-fluoroprop-1-ene

N-(diphenylmethylene)glycine tert-butyl ester

Downstream raw materials:

DL-asparagine

Refernces

• 1、 Laue, Klaus W.,Haufe, Guenter. "3-Bromo-2-fluoropropene - a fluorinated building block. 2-fluoroallylation of glycine and alanine ester imines". . p. 1453 - 1456. Retrieved 2007/10/03.