Tetrahydrofuran → HCID 86632863, compound

HRID 1628397Notes

Reaction equation

HRID 1628397 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])[CH3:3].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21].C(N(CC)CC)C.O1CCCC1>C(OCC)(=O)C>[N+:17]([C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:20]([O-:22])=[O:21])[C:11]=1[NH:8][CH2:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:9])([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471Triethylamine2×HCID 118141-Chloro-2,6-dinitrobenzeneHCID 458475beta-Alanine, ethyl ester, hydrochloride2×

Product 1

HCID 86632863HCID 86632863, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of beta-alanine ethyl ester hydrochloride (911 mg, 5.39 mmol), 2-chloro-1,3-dinitrobenzene (1.00 g, 4.94 mmol), triethylamine (2.07 mL, 14.9 mmol) and tetrahydrofuran (50 mL) was stirred at room temperature for 2 hr. To the reaction mixture were added beta-alanine ethyl ester hydrochloride (455 mg, 2.96 mmol) and triethylamine (1.03 mL, 7.39 mmol) at room temperature and the resultant mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 0-20% ethyl acetate/n-hexane gradient mixture to give the title compound as an oil (1.39 g, 4.92 mmol, 99.6%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 0-20% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-623b65e31a1a4f17bc4abd0f6bb2c025
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

Loading…