Cesium carbonate → HCID 59300715, compound

HRID 1675274Notes

Reaction equation

HRID 1675274 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 59300715HCID 59300715, compoundYield 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-e2d3224def3746508edd7a7f6aef2034
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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