Cesium carbonate → 3-((4-((S)-3-((S)-4-Benzyl-2-oxooxazolidin-3-yl)-1-(isoxazol-3-yl)-3-oxopropyl)phenoxy)methyl)phenylboronic acid

HRID 2235614Notes

Reaction equation

HRID 2235614 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:29])[CH2:15][C@@H:16]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[C:17]1[CH:21]=[CH:20][O:19][N:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:31][C:32]1[CH:33]=[C:34]([B:38]([OH:40])[OH:39])[CH:35]=[CH:36][CH:37]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:29])[CH2:15][C@@H:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:31][C:32]2[CH:33]=[C:34]([B:38]([OH:40])[OH:39])[CH:35]=[CH:36][CH:37]=2)=[CH:24][CH:23]=1)[C:17]1[CH:21]=[CH:20][O:19][N:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27732813-(Bromomethyl)benzeneboronic acidHCID 57801829(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

Product 1

HCID 593007153-((4-((S)-3-((S)-4-Benzyl-2-oxooxazolidin-3-yl)-1-(isoxazol-3-yl)-3-oxopropyl)phenoxy)methyl)phenylboronic acidYield 17.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The phenol (7.5) (400 mg, 1.02 mmol) and 3-(bromomethyl)phenylboronic acid (219 mg, 1.02 mmol) were dissolved in DMF (10 mL). Cesium carbonate (664 mg, 2.04 mmol) was added to the mixture, and the slurry was stirred for 48 hours. The reaction was then diluted with water and extracted with EtOAc (2×100 mL). The organic layers were combined and washed with a 1 M lithium chloride solution (1×50 mL) and brine (1×50 mL), and dried over magnesium sulfate. The filtrate was concentrated, and the residue was purified by medium pressure chromatography (silica gel, 30 to 100% EtOAc:hexanes) to give 34.1 (95.0 mg). MS ESI (pos.) m/e: 527.2 (M+H).

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. washwashed with a 1 M lithium chloride solution (1×50 mL) and brine (1×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by medium pressure chromatography (silica gel, 30 to 100% EtOAc:hexanes)

Sources & evidence

ORD record
ord-3adb2f0e7d1247a4bb335f85c877b562
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

Loading…