Potassium Carbonate → HCID 67279997, compound

HRID 1693291Notes

Reaction equation

HRID 1693291 reaction equation
C([O:4][C:5]1[C:14]2[CH2:13][S:12][N:11]=[C:10]([N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]3=[N:30][N:31]([CH2:33][C:34]4[C:39]([CH3:40])=[C:38]([O:41][CH3:42])[C:37]([CH3:43])=[CH:36][N:35]=4)[N:32]=[C:7]([C:8]=23)[CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CO>[CH3:42][O:41][C:38]1[C:37]([CH3:43])=[CH:36][N:35]=[C:34]([CH2:33][N:31]2[N:32]=[C:7]3[CH2:6][C:5](=[O:4])[C:14]4[CH2:13][S:12][N:11]=[C:10]([N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:9]([C:8]=43)=[N:30]2)[C:39]=1[CH3:40]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 67280305HCID 67280305, compound

Product 1

HCID 67279997HCID 67279997, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl acetate of Example 39 (507 mg), methanol (12 mL) and potassium carbonate (57 mg) was stirred under cooling in an ice bath for 30 minutes. After confirming that the raw material disappeared, a saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound (430 mg, 91%) as an oil.

Workup

  1. temperatureunder cooling in an ice bath for 30 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-011012b7a69441b08cada0da0f50b908
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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