Sodium Bicarbonate → HCID 24880181, compound

HRID 445432Notes

Reaction equation

HRID 445432 reaction equation
Cl.[NH2:2][C@:3]([CH3:27])([CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[CH:11][C:10]=1[Cl:26])[CH2:4][OH:5].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[NH2:2][C@:3]([CH3:27])([CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=2)=[CH:11][C:10]=1[Cl:26])[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67106091HCID 67106091, compound

Product 1

HCID 24880181HCID 24880181, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of Example 27 (9.3 g) in ethyl acetate (450 mL) was added saturated aqueous sodium hydrogen carbonate solution (450 mL), and the resultant solution was stirred at room temperature for 10 minutes. The organic layer was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the resultant residue was purified by NH-silica gel column chromatography (ethyl acetate:methanol=4:1) to obtain the target product (8.9 g) as a white powder.

Workup

  1. washThe organic layer was washed with water and saturated brine in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. customthe resultant residue was purified by NH-silica gel column chromatography (ethyl acetate:methanol=4:1)

Sources & evidence

ORD record
ord-71e19b596bec4e17936c7415dae7af0f
Source dataset
uspto-grants-2013_07
Patent number
US08476305B2

Reaction notes

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