Sodium Hydroxide → HCID 178418957, compound

HRID 9877Notes

Reaction equation

HRID 9877 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]3(O)[CH2:21][CH:20]4[N:16]([CH2:17][CH2:18][CH2:19]4)[CH2:15][CH2:14]3)[C:9]=2[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]3[CH2:21][CH:20]4[N:16]([CH2:17][CH2:18][CH2:19]4)[CH2:15][CH:14]=3)[C:9]=2[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178419037HCID 178419037, compound

Product 1

HCID 178418957HCID 178418957, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The compound prepared as described in Example 2 (720 mg, 1.90 mmol) was dissolved in concentrated hydrochloric acid (14 ml). The resulting solution was heated under reflux for 8 hours. At the end of this time, the reaction mixture was neutralized with an aqueous solution of 1 N sodium hydroxide, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent, ethyl acetate:methanol:isopropylamine=10:1:1), to give the title compound (Rf=0.45, 255 mg) as a white powder (yield 37%).

Workup

  1. customThe compound prepared
  2. temperatureThe resulting solution was heated
  3. temperatureunder reflux for 8 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by column chromatography through silica gel (eluent, ethyl acetate:methanol:isopropylamine=10:1:1)

Sources & evidence

ORD record
ord-f2d7cc9ea376403b8f04a982db70e925
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Reaction notes

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