Dichloromethane → HCID 58484727, compound

HRID 1803961Notes

Reaction equation

HRID 1803961 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].[CH2:14]([C@@H:21]1[CH2:25][O:24][C:23](=[O:26])[NH:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)Cl.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH2:14]([C@@H:21]1[CH2:25][O:24][C:23](=[O:26])[N:22]1[C:8]1[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27343694-Methoxycarbonylphenylboronic acidHCID 2734969(R)-4-Benzyl-2-oxazolidinone

Product 1

HCID 58484727HCID 58484727, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

To a mixture of p-(methoxycarbonyl)phenylboronic acid (2.45 g), (R)-4-benzyloxazolidin-2-one (1.205 g) and copper (II) acetate (1.23 g) were added methylene chloride (20 mL) and triethylamine (1.9 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and insoluble materials were filtered off. The filtrate was extracted with chloroform. The solvent was evaporated, and the obtained residue was purified by column chromatography (chloroform) to give the title compound (0.19 g).

Workup

  1. filtrationwere filtered off
  2. extractionThe filtrate was extracted with chloroform
  3. customThe solvent was evaporated
  4. customthe obtained residue was purified by column chromatography (chloroform)

Sources & evidence

ORD record
ord-4c382d2c78fb4ef0a371414e1d806d39
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

Loading…