2-(S)-[N-(tert-butoxycarbonyl)amino]-3-methylbutanal

Base Information

• Chemical Name: 2-(S)-[N-(tert-butoxycarbonyl)amino]-3-methylbutanal
• CAS No.: 123285-52-9
• Molecular Formula: C₁₀H₁₉NO₃
• Molecular Weight: 201.266
• Mol file: 123285-52-9.mol

Synonyms:2-(S)-[N-(tert-butoxycarbonyl)amino]-3-methylbutanal

Chemical Property of 2-(S)-[N-(tert-butoxycarbonyl)amino]-3-methylbutanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(S)-[N-(tert-butoxycarbonyl)amino]-3-methylbutanal

There total 12 articles about 2-(S)-[N-(tert-butoxycarbonyl)amino]-3-methylbutanal 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: 80.0%

N-Boc-(S/R)-valine (13734-41-3,22838-58-0,54895-12-4) → 2-(S)-[N-(tert-butoxycarbonyl)amino]-3-methylbutanal (123285-52-9)

Guidance literature:

N-Boc-(S/R)-valine; With 1,1'-carbonyldiimidazole; In dichloromethane; at -78 - 0 ℃; for 1.33333h; Inert atmosphere; Schlenk technique;

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.202102204

Reference yield: 71.0%

rac-tert-butyl (1-hydroxy-3-methylbutan-2-yl)carbamate (169556-48-3) → 2-(S)-[N-(tert-butoxycarbonyl)amino]-3-methylbutanal (123285-52-9)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; for 0.5h; Reflux;

DOI:10.1021/acs.orglett.6b02123

Reference yield:

rac-tert-butyl (1-hydroxy-3-methylbutan-2-yl)carbamate (169556-48-3) → 2-tert-butoxycarbonylamino-3-methyl-butyric acid 2-tert-butoxycarbonylamino-3-methyl-butyl ester + 2-(S)-[N-(tert-butoxycarbonyl)amino]-3-methylbutanal (123285-52-9)

Guidance literature:

With oxygen; tetrabutylammonium acetate; triethylamine; palladium diacetate; In tetrahydrofuran; at 20 ℃; for 16h; Title compound not separated from byproducts;

DOI:10.1021/jo0482211

upstream raw materials:

tert-butyl 1-(methoxy(methyl)amino)-3-methyl-1-oxobutan-2-ylcarbamate

rac-tert-butyl (1-hydroxy-3-methylbutan-2-yl)carbamate

N-Boc-(S/R)-valine

N-Boc-valine methyl ester

Downstream raw materials:

C₂₅H₂₇N₃O₆S

C₂₅H₂₉N₃O₆S

α-[2,2-bis(phenylsulfonyl)ethyl]-α-(tert-butoxycarbonylamino)-β-methylbutanal

2-isopropyl-5-(9-phenyl-9H-fluoren-9-yl)-5,6-dihydro-4H-pyrrolo[3,4-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Refernces

• 1、 Bartoszak-Adamska, El?bieta,Go?dyn, Mateusz,Koroniak, Henryk,Koroniak-Szejn, Katarzyna,Salamon-Krokosz, Katarzyna,Siod?a, Tomasz. "Fluorinated Olefinic Lactams: The Case of Amino Acids - Preparation and Mechanistic Studies". . . Retrieved 2022/03/17.
• 2、 Ivkovic, Jakov,Lembacher-Fadum, Christian,Breinbauer, Rolf. "A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H". . p. 10456 - 10460. Retrieved 2015/11/10.