Sodium Hydroxide → HCID 136388337, compound

HRID 1861935Notes

Reaction equation

HRID 1861935 reaction equation
C[O:2][C:3](=[O:27])[CH:4]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH2:26])=[N:22][N+:23]([O-:25])=[O:24])=[CH:16][CH:15]=1)[CH2:5][NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[OH-].[Na+]>CO>[C:10]([O:9][C:7]([NH:6][CH2:5][CH:4]([C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([NH2:26])=[N:22][N+:23]([O-:25])=[O:24])=[CH:18][CH:19]=1)[C:3]([OH:27])=[O:2])=[O:8])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136388338HCID 136388338, compound

Product 1

HCID 136388337HCID 136388337, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the compound (0.42 g) obtained in Example 220, 2 N aqueous sodium hydroxide solution (0.6 ml) and methanol (10 ml) was stirred at room temperature for 5 h. The reaction mixture was concentrated under reduced pressure and a 5% aqueous citric acid solution and ethyl acetate were added to the residue. The organic layer was washed with water, dried and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, methanol:methylene chloride=5:95) to give 0.34 g of the titled compound (yield, 84%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona 5% aqueous citric acid solution and ethyl acetate were added to the residue
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent, methanol:methylene chloride=5:95)

Sources & evidence

ORD record
ord-35ea943b1b824161aed74720e3d373ac
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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