Potassium Hydroxide → HCID 117833949, compound

HRID 515927Notes

Reaction equation

HRID 515927 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:16]([C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=3[C:30]([N:32]3[C@H:41]([CH2:42][O:43][CH2:44][CH2:45][N:46]4[CH2:51][CH2:50][O:49][CH2:48][CH2:47]4)[CH2:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:33]3)=[O:31])[N:20]([CH3:52])[C:19]=2[CH3:53])=[O:17])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[OH-].[K+].C(=O)(O)[O-].[Na+]>CO>[ClH:29].[Cl:29][C:27]1[CH:26]=[CH:25][C:24]([C:30]([N:32]2[C@H:41]([CH2:42][O:43][CH2:44][CH2:45][N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])=[C:23]([C:21]2[N:20]([CH3:52])[C:19]([CH3:53])=[C:18]([C:16]([N:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)=[O:17])[CH:22]=2)[CH:28]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 131733325HCID 131733325, compound

Product 1

HCID 117833949HCID 117833949, compoundYield 168.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 0.7 g of the compound of Step D in 5 mL of methanol there is added 0.92 mL of a 1M solution of potassium hydroxide in methanol. After stirring for 1 hour 10 minutes at ambient temperature, saturated aqueous sodium bicarbonate solution is added. The product which precipitates is extracted with ethyl acetate and then washed with water and brine. The resulting aqueous phases are extracted again with ethyl acetate. The organic phases thereby obtained are dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product obtained is purified by chromatography over silica gel using dichloromethane and ammonia-in-ethanol as eluants to provide 0.536 g of the title product, in the form of the base. The latter is dissolved in acetonitrile and converted into salt form using 1M aqueous HCl solution. After a lyophilisation step, the expected product is obtained in the form of a solid.

Workup

  1. customThe product which precipitates
  2. extractionis extracted with ethyl acetate
  3. washwashed with water and brine
  4. extractionThe resulting aqueous phases are extracted again with ethyl acetate
  5. customThe organic phases thereby obtained
  6. dry with materialare dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product obtained
  10. customis purified by chromatography over silica gel

Sources & evidence

ORD record
ord-6ebc411124a04ce8a38cb1dc8f5f7942
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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