(Dibenzylamino)acetic acid tert-butyl ester

Base Information

• Chemical Name: (Dibenzylamino)acetic acid tert-butyl ester
• CAS No.: 94226-56-9
• Molecular Formula: C20H25NO2
• Molecular Weight: 311.424
• DSSTox Substance ID: DTXSID701218506
• Nikkaji Number: J1.230.790J
• Mol file: 94226-56-9.mol

Synonyms:DTXSID701218506;AKOS008716554;(Dibenzylamino)acetic acid tert-butyl ester;N,N-Bis(phenylmethyl)glycine 1,1-dimethylethyl ester;94226-56-9

Chemical Property of (Dibenzylamino)acetic acid tert-butyl ester

Chemical Property:

• PSA: 29.54000
• LogP: 4.03050
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 311.188529040
• Heavy Atom Count: 23
• Complexity: 329

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CN(CC1=CC=CC=C1)CC2=CC=CC=C2

Technology Process of (Dibenzylamino)acetic acid tert-butyl ester

There total 2 articles about (Dibenzylamino)acetic acid tert-butyl ester 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: 100.0%

bromoacetic acid tert-butyl ester (5292-43-3) + dibenzylamine (103-49-1) → tert-butyl 2-(dibenzylamino)ethanoate (94226-56-9)

Guidance literature:

In 1,4-dioxane; ethanol; for 4h; Heating;

DOI:10.1021/ol030085j

Reference yield: 98.0%

acetic acid tert-butyl ester (540-88-5) + N,N-dibenzyl-O-benzoylhydroxylamine (52742-32-2) → tert-butyl 2-(dibenzylamino)ethanoate (94226-56-9)

Guidance literature:

acetic acid tert-butyl ester; With bis(2,2,6,6-tetramethyl-1-piperidyl)zinc; In toluene; at 20 ℃; for 1h; Microwave irradiation;

N,N-dibenzyl-O-benzoylhydroxylamine; With [2,2]bipyridinyl; copper dichloride; In tetrahydrofuran; toluene; at 20 ℃; for 1h; Microwave irradiation;

DOI:10.1039/c3cc49296f

Reference yield: 99.0%

tert-butyl 2-(dibenzylamino)ethanoate (94226-56-9) + 1-[chloro(p-tolylsulfinyl)methylidene]cyclobutane (854139-13-2) → tert-butyl (1-[chloro(p-tolylsulfinyl)methyl]cyclobutyl)-N,N-dibenzylaminoacetate (1268616-69-8)

Guidance literature:

tert-butyl 2-(dibenzylamino)ethanoate; With lithium diisopropyl amide; In tetrahydrofuran;

1-[chloro(p-tolylsulfinyl)methylidene]cyclobutane; In tetrahydrofuran; at -45 ℃; for 1h;

DOI:10.1016/j.tet.2010.12.023

upstream raw materials:

bromoacetic acid tert-butyl ester

dibenzylamine

acetic acid tert-butyl ester

N,N-dibenzyl-O-benzoylhydroxylamine

Downstream raw materials:

Dibenzyl-((Z)-2-tert-butoxy-2-trimethylsilanyloxy-vinyl)-amine

(Z)-tert-butoxy-2-(dibenzylamino)-1-(trimethylsiloxy)ethylene

2-Dibenzylamino-3-hydroxy-nonanoic acid tert-butyl ester

(2S,3R)-3-Butyl-2-dibenzylamino-pentanedioic acid 1-tert-butyl ester 5-ethyl ester

Refernces

• 1、 Boutard, Nicolas,Labeguere, Frederic,Vidal, Yves,Lavergne, Jean-Pierre,Martinez, Jean. "New C-glycosylated α-amino acid synthesis by addition reaction of an amino acid organozinc reagent on carbohydrate-derived aldehydes". experimental part. p. 1461 - 1471. Retrieved 2012/05/05.
• 2、 Yamashita, Ayako,Norton, Emily B.,Williamson, R. Thomas,Ho, Douglas M.,Sinishtaj, Sandra,Mansour, Tarek S.. "Use of bis-(chiral α-methylbenzyl)glycine esters for synthesis of enantiopure β-hydroxyamino esters". . p. 3305 - 3308. Retrieved 2007/10/03.