Sodium Hydroxide → HCID 59009182, compound

HRID 545125Notes

Reaction equation

HRID 545125 reaction equation
C(OC([CH:8](C(OC(C)(C)C)=O)[C:9]1[N:14]=[N:13][C:12]([S:15][CH2:16][C:17]([NH:19][CH2:20][C@@H:21]2[O:26][CH2:25][CH2:24][N:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=3)[CH2:22]2)=[O:18])=[CH:11][CH:10]=1)=O)(C)(C)C.[OH-].[Na+]>FC(F)(F)C(O)=O.[Cl-].[Na+].O>[Cl:35][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[Cl:34])[CH2:27][N:23]1[CH2:24][CH2:25][O:26][C@@H:21]([CH2:20][NH:19][C:17](=[O:18])[CH2:16][S:15][C:12]2[N:13]=[N:14][C:9]([CH3:8])=[CH:10][CH:11]=2)[CH2:22]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616378HCID 86616378, compound

Product 1

HCID 59009182HCID 59009182, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The resultant product (940 mg) of (217-3) was dissolved in trifluoroacetic acid (6 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was adjusted to pH=4 with a 1 mol/L aqueous sodium hydroxide solution. Saturated brine was added to the obtained solution, and the mixture was extracted with a mixed solvent of chloroform-methanol. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (265 mg) as a white solid.

Workup

  1. extractionthe mixture was extracted with a mixed solvent of chloroform-methanol
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography
  5. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-4b19c57f85de482499c60a910f277931
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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