(S)-4-(tert-Butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole

Base Information

• Chemical Name: (S)-4-(tert-Butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole
• CAS No.: 199277-80-0
• Molecular Formula: C₁₃H₁₈N₂O
• Molecular Weight: 218.299
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70452618
• Nikkaji Number: J910.654E
• Wikidata: Q72502945
• Mol file: 199277-80-0.mol

Synonyms:199277-80-0;(S)-4-(tert-Butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole;(4S)-4-tert-butyl-2-(6-methylpyridin-2-yl)-4,5-dihydro-1,3-oxazole;(S)-2-[4-(1,1-Dimethylethyl)-4,5-dihydro-2-oxazolyl]-6-methylpyridine;2-[(4S)-4-tert-Butyl-4,5-dihydro-1,3-oxazol-2-yl]-6-methylpyridine;DTXSID70452618;NHWBZSGKOQHPDW-LLVKDONJSA-N;AMY13837;Pyridine, 2-[(4S)-4-(1,1-dimethylethyl)-4,5-dihydro-2-oxazolyl]-6-methyl-;BS-49671;E78019;A911300;(4S)-2-(6-Methyl-2-pyridyl)-4-tert-butyl-2-oxazoline;2-[(4S)-4-(TERT-BUTYL)-4,5-DIHYDRO-2-OXAZOLYL]-6-METHYLPYRIDINE

Chemical Property of (S)-4-(tert-Butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.551
• Boiling Point: 328.755 °C at 760 mmHg
• PKA: 3.83±0.19(Predicted)
• Flash Point: 152.626 °C
• PSA: 34.48000
• Density: 1.077 g/cm³
• LogP: 2.01710
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 218.141913202
• Heavy Atom Count: 16
• Complexity: 280

Purity/Quality:

99% ^*data from raw suppliers

(S)-4-(tert-Butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC(=CC=C1)C2=NC(CO2)C(C)(C)C
• Isomeric SMILES: CC1=NC(=CC=C1)C2=N[C@H](CO2)C(C)(C)C

Technology Process of (S)-4-(tert-Butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole

There total 4 articles about (S)-4-(tert-Butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole 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: 84.0%

methyl 6-methylpicolinimidate (129821-92-7) + (S)-tert-leucinol (112245-13-3) → (S)-4-(tert-butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole (199277-80-0,2491654-89-6)

Guidance literature:

at 65 ℃; for 16h; Inert atmosphere;

DOI:10.1021/om4001549

Reference yield: 55.0%

2-Cyano-6-methylpyridine (1620-75-3) + (S)-tert-leucinol (112245-13-3) → (S)-4-(tert-butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole (199277-80-0,2491654-89-6)

Guidance literature:

2-Cyano-6-methylpyridine; With zinc trifluoromethanesulfonate; In toluene; for 0.0833333h; Schlenk technique; Glovebox; Inert atmosphere;

(S)-tert-leucinol; In toluene; for 24h; Schlenk technique; Glovebox; Inert atmosphere; Reflux;

DOI:10.1021/acs.organomet.9b00067

Reference yield:

L-tert-Leucine (20859-02-3) → (S)-4-(tert-butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole (199277-80-0,2491654-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate; iodine / tetrahydrofuran / 15 h / Inert atmosphere; Schlenk technique; Reflux

1.2: 5 h / Inert atmosphere; Schlenk technique

2.1: toluene-4-sulfonic acid / toluene / 1 h / 80 °C / Inert atmosphere; Schlenk technique

With sodium tetrahydroborate; iodine; toluene-4-sulfonic acid; In tetrahydrofuran; toluene;

DOI:10.1021/acs.orglett.9b03338

upstream raw materials:

2-Cyano-6-methylpyridine

(S)-tert-leucinol

methyl 6-methylpicolinimidate

L-tert-Leucine

Downstream raw materials:

(S)-2-(6-benzhydrylpyridin-2-yl)-4-(tert-butyl)-4,5-dihydrooxazole

(S)-2-(6-benzylpyridin-2-yl)-4-(tert-butyl)-4,5-dihydrooxazole

Refernces

• 1、 -. "Phosphine pyridine oxazoline compound, metal complex, and preparation method and application thereof". Paragraph 0141-0146. . Retrieved 2020/10/04.
• 2、 De Crisci, Antonio G.,Chung, Kevin,Oliver, Allen G.,Solis-Ibarra, Diego,Waymouth, Robert M.. "Chemoselective oxidation of polyols with chiral palladium catalysts". . p. 2257 - 2266. Retrieved 2013/05/21.