Chloroform → HCID 118194560, compound

HRID 1775774Notes

Reaction equation

HRID 1775774 reaction equation
[C:1](/[C:4](=[CH:23]\[C:24](\[CH3:39])=[CH:25]\[CH:26]([CH3:38])[CH2:27][CH:28]([CH3:37])[CH2:29][CH:30]([CH3:36])[CH2:31][CH:32]([CH3:35])[CH2:33][CH3:34])/[CH2:5][CH:6]([CH3:22])[C:7]([O:9][CH:10]1C(=O)OC(C(O)=O)C1C(O)=O)=[O:8])([OH:3])=[O:2].[C:40](=[O:43])([O-:42])O.[Na+].[C:45]([O:48][CH2:49]Br)(=[O:47])[CH3:46].[Cl-].[NH4+].[CH:53](Cl)(Cl)Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:22][CH:6]([CH2:5]/[C:4](=[CH:23]/[C:24](/[CH3:39])=[CH:25]/[CH:26]([CH3:38])[CH2:27][CH:28]([CH3:37])[CH2:29][CH:30]([CH3:36])[CH2:31][CH:32]([CH3:35])[CH2:33][CH3:34])/[C:1]([O:3][CH2:49][O:48][C:45](=[O:47])[CH3:46])=[O:2])[C:7]([O:9][CH2:10][O:42][C:40](=[O:43])[CH3:53])=[O:8]

Participants

8

Reactant 5

HCID 6212ChloroformHCID 25517Ammonium ChlorideHCID 68536Bromomethyl acetateHCID 516892Sodium BicarbonateHCID 72700712HCID 72700712, compound

Product 1

HCID 118194560HCID 118194560, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

To Compound 1 (130 mg, 0.235 mmol), water (10 mL), sodium hydrogen carbonate (200 mg, 2.33 mmol), chloroform (5 mL), tetrabutylammonium hydrogen sulfate (80 mg, 0.235 mmol), and bromomethyl acetate (0.120 mL, 1.22 mmol) were added, and the resulting mixture was vigorously stirred at room temperature for 3 hours. To the reaction mixture, a saturated aqueous ammonium chloride solution was added, and the resulting mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then, the solvent was evaporated under reduced, pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate), whereby Compound 27 (31.9 mg, 18%) and Compound 29 (23.9 mg, 19%) were obtained, respectively.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate), whereby Compound 27 (31.9 mg, 18%)

Sources & evidence

ORD record
ord-c746e8ac44794297be4c611a943e769b
Source dataset
uspto-grants-2016_02
Patent number
US09260459B2

Reaction notes

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