Sodium Bicarbonate → HCID 58065503, compound

HRID 1964548Notes

Reaction equation

HRID 1964548 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:35])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]3[O:29][CH:30]([CH2:33]O)[CH2:31][N:32]=3)=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1.COCCN(S(F)(F)[F:46])CCOC.C(=O)([O-])O.[Na+]>ClCCl>[F:46][CH2:33][CH:30]1[O:29][C:28]([C:26]2[NH:27][C:23]([C:8]3[CH:9]=[C:10]([O:12][C:13]4[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=4)[CH:11]=[C:6]([O:5][C@@H:4]([CH3:35])[CH2:3][O:2][CH3:1])[CH:7]=3)=[CH:24][CH:25]=2)=[N:32][CH2:31]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58065449HCID 58065449, compound

Product 1

HCID 58065503HCID 58065503, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-4,5-dihydro-1,3-oxazol-5-yl]methanol (100 mg, 0.20 mmol) synthesized in Example 29 was dissolved in dichloromethane (5 mL), and bis(2-methoxyethyl)aminosulfur trifluoride (81 μL, 0.44 mmol) was added at 0° C. After stirring at room temperature for 6 hours, a saturated aqueous sodium hydrogencarbonate solution was added, and extraction was carried out with dichloromethane (60 mL). The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=80%-100%) to afford the desired product (61 mg, yield 61%) as a white solid.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=80%-100%)

Sources & evidence

ORD record
ord-665127410fac4760ab420fcce8487385
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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