Cesium carbonate → HCID 69387399, compound

HRID 916840Notes

Reaction equation

HRID 916840 reaction equation
[CH3:1][C:2]1([CH3:27])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:34]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH2:45][CH2:46][CH2:47]Br)[CH:39]=1)(=[O:36])[CH3:35]>CN(C=O)C>[C:34]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH2:45][CH2:46][CH2:47][O:26][C:23]2[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][N:14]3[CH2:13][C@@H:12]([C:10]4[CH:9]=[CH:8][C:6]5[O:7][C:2]([CH3:27])([CH3:1])[O:3][CH2:4][C:5]=5[CH:11]=4)[O:16][C:15]3=[O:17])=[CH:25][CH:24]=2)[CH:39]=1)(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 69384373HCID 69384373, compoundHCID 69385416HCID 69385416, compound

Product 1

HCID 69387399HCID 69387399, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-hydroxyphenyl)ethyl]-1,3-oxazolidin-2-one (Example 28 v) (37 mg) in dry DMF (0.4 mL) was treated with caesium carbonate (65 mg) and 3-(4bromobutyl)phenyl acetate (0.2 mmol) as a solution in DMF (0.5 mL). Further DMF was added (1 mL) and the reaction mixture stirred at 50° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated in vacuo in a genevac. The residue was suspended in chloroform and filtered to remove inorganic salts. The filtrate was added to the top of a pre-conditioned NH2 propyl cartridge (1 g). The cartridge was washed with chloroform and methanol and the title compound eluted with 2M NH3-MeOH. LCMS RT=3.86 min

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo in a genevac
  3. filtrationfiltered
  4. customto remove inorganic salts
  5. additionThe filtrate was added to the top of a pre-conditioned NH2 propyl cartridge (1 g)
  6. washThe cartridge was washed with chloroform and methanol
  7. washthe title compound eluted with 2M NH3-MeOH

Sources & evidence

ORD record
ord-9dae8d3e15504d55b2233dfc03be9015
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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