tert-butyl N-(diphenylmethylidene)-2-nitro-5-(trifluoromethyl)-L-phenylalaninate

Base Information

• Chemical Name: tert-butyl N-(diphenylmethylidene)-2-nitro-5-(trifluoromethyl)-L-phenylalaninate
• CAS No.: 1290617-52-5
• Molecular Formula: C₂₇H₂₅F₃N₂O₄
• Molecular Weight: 498.502
• Mol file: 1290617-52-5.mol

Synonyms:tert-butyl N-(diphenylmethylidene)-2-nitro-5-(trifluoromethyl)-L-phenylalaninate

Chemical Property of tert-butyl N-(diphenylmethylidene)-2-nitro-5-(trifluoromethyl)-L-phenylalaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl N-(diphenylmethylidene)-2-nitro-5-(trifluoromethyl)-L-phenylalaninate

There total 4 articles about tert-butyl N-(diphenylmethylidene)-2-nitro-5-(trifluoromethyl)-L-phenylalaninate 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: 72.0%

2-(bromomethyl)-1-nitro-4-(trifluoromethyl)benzene (133605-28-4) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → tert-butyl N-(diphenylmethylidene)-2-nitro-5-(trifluoromethyl)-L-phenylalaninate (1290617-52-5)

Guidance literature:

With (-)-(O)-⁽⁹⁾-allyl-N-(9-anthracenylmethyl)cinchodinium bromide; caesium hydroxide monohydrate; In dichloromethane; at -30 ℃; for 18h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/jo200530j

Reference yield:

2-nitro-5-(trifluoromethyl)benzaldehyde (1176723-57-1) → tert-butyl N-(diphenylmethylidene)-2-nitro-5-(trifluoromethyl)-L-phenylalaninate (1290617-52-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 - 20 °C

2: carbon tetrabromide; triphenylphosphine / dichloromethane / 16 h / 20 °C

3: caesium hydroxide monohydrate; (-)-(O)-⁽⁹⁾-allyl-N-(9-anthracenylmethyl)cinchodinium bromide / dichloromethane / 18 h / -30 °C

With sodium tetrahydroborate; (-)-(O)-⁽⁹⁾-allyl-N-(9-anthracenylmethyl)cinchodinium bromide; caesium hydroxide monohydrate; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo200530j

Reference yield:

C8H6F3NO3 (1227604-33-2) → tert-butyl N-(diphenylmethylidene)-2-nitro-5-(trifluoromethyl)-L-phenylalaninate (1290617-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1: carbon tetrabromide; triphenylphosphine / dichloromethane / 16 h / 20 °C

2: caesium hydroxide monohydrate; (-)-(O)-⁽⁹⁾-allyl-N-(9-anthracenylmethyl)cinchodinium bromide / dichloromethane / 18 h / -30 °C

With (-)-(O)-⁽⁹⁾-allyl-N-(9-anthracenylmethyl)cinchodinium bromide; caesium hydroxide monohydrate; carbon tetrabromide; triphenylphosphine; In dichloromethane;

DOI:10.1021/jo200530j

upstream raw materials:

2-(bromomethyl)-1-nitro-4-(trifluoromethyl)benzene

N-(diphenylmethylene)glycine tert-butyl ester

2-nitro-5-(trifluoromethyl)benzaldehyde

C₈H₆F₃NO₃

Downstream raw materials:

2-nitro-5-(trifluoromethyl)-L-phenylalanine

Refernces

• 1、 McAllister, Laura A.,Bechle, Bruce M.,Dounay, Amy B.,Evrard, Edelweiss,Gan, Xinmin,Ghosh, Somraj,Kim, Ji-Young,Parikh, Vinod D.,Tuttle, Jamison B.,Verhoest, Patrick R.. "A general strategy for the synthesis of cyclic N-aryl hydroxamic acids via partial nitro group reduction". experimental part. p. 3484 - 3497. Retrieved 2011/06/24.