1,2-Dibromoethane → (S)-4-Benzyl-3-((S)-3-(4-(2-bromoethoxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

HRID 1675291Notes

Reaction equation

HRID 1675291 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:30][CH2:31][CH2:32]Br.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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][CH2:32][CH2:31][Br:30])=[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 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 57801829(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

Product 1

HCID 59300638(S)-4-Benzyl-3-((S)-3-(4-(2-bromoethoxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-oneYield 39.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A mixture of 7.5 (200 mg, 0.51 mmol), 1,2-dibromoethane (0.88 mL, 10 mmol), potassium carbonate (210 mg, 1.5 mmol) and tetrabutylammonium bromide (16 mg, 51 μmol) in water (6.0 mL) was heated to reflux and stirred for two hours. The mixture was then cooled to room temperature and extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by medium pressure chromatography (silica gel, 20 to 100% EtOAc:hexanes) to obtain 47.1 (100 mg). MS ESI (pos.): m/e 500.0 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by medium pressure chromatography (silica gel, 20 to 100% EtOAc:hexanes)

Sources & evidence

ORD record
ord-8bb2c64eb2014f44816feaf48d215946
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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