Sodium Bicarbonate → HCID 58398479, compound

HRID 1879411Notes

Reaction equation

HRID 1879411 reaction equation
[Si]([O:18][CH2:19][C@H:20]([CH3:62])[CH2:21][N:22]([S:53]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=1)(=[O:55])=[O:54])[C:23]1[CH:40]=[C:39]([C:41]2C=CC=CC=2)[C:38]([C:47]2C=CC=CC=2)=[CH:37][C:24]=1[O:25][CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C(=O)([O-])O.[Na+]>C1COCC1>[OH:18][CH2:19][C@H:20]([CH3:62])[CH2:21][N:22]([S:53]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=1)(=[O:55])=[O:54])[C:23]1[CH:40]=[C:39]([CH3:41])[C:38]([CH3:47])=[CH:37][C:24]=1[O:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11078149TBAF tetrahydrofuranHCID 67106218HCID 67106218, compound

Product 1

HCID 58398479HCID 58398479, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

840 mg of methyl 4-[(2-{[(2R)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropyl](pyridin-2-ylsulfonyl)amino}-4,5-diphenylphenoxy)methyl]benzoate was dissolved in 8.40 mL of THF, and 0.554 mL of a 1 M tetrabutyl ammonium fluoride/THF solution was added thereto at room temperature, followed by stirring at room temperature for 2 hours. To the reaction liquid was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:40 to 0:100) to obtain 468 mg of methyl 4-[(2-{[(2R)-3-hydroxy-2-methylpropyl](pyridin-2-ylsulfonyl)amino}-4,5-dimethylphenoxy)methyl]benzoate.

Workup

  1. customat room temperature
  2. customTo the reaction liquid
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:40 to 0:100)

Sources & evidence

ORD record
ord-fae7b7663b5f4a578b4bcc8d24a9460b
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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