Sodium Hydroxide → HCID 118113200, compound

HRID 1485128Notes

Reaction equation

HRID 1485128 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:29]=[CH:28][C:9]([CH2:10][N:11]3[CH2:16][CH2:15][C:14]([OH:17])=[C:13]([C:18]([NH:20][CH2:21][C:22]([O:24]CC)=[O:23])=[O:19])[C:12]3=[O:27])=[CH:8][C:7]=2[CH3:30])[CH2:3][CH2:2]1.[OH-].[Na+:32]>C(O)C>[Na+:32].[CH:1]1([CH2:4][O:5][C:6]2[CH:29]=[CH:28][C:9]([CH2:10][N:11]3[CH2:16][CH2:15][C:14]([OH:17])=[C:13]([C:18]([NH:20][CH2:21][C:22]([O-:24])=[O:23])=[O:19])[C:12]3=[O:27])=[CH:8][C:7]=2[CH3:30])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118113269HCID 118113269, compound

Product 1

HCID 118113200HCID 118113200, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution in ethanol (37.8 mL) of the compound (1.97 g) obtained in step (1) above, 0.5 mol/L sodium hydroxide in aqueous solution (18.9 mL) was added under cooling with ice and the mixture was brought to room temperature at which it was stirred for 15 minutes. After the reaction mixture was concentrated under reduced pressure, the resulting residue was purified by DIAION (registered trademark) HP20 column chromatography (with elution by methanol). The eluted fraction was concentrated under reduced pressure and to a solution of the resulting compound in water (2 mL), acetone (100 mL) was added and the mixture was stirred at room temperature for an hour. The precipitate was recovered by filtration to give the titled compound as a colorless solid (1.60 g).

Workup

  1. temperatureunder cooling with ice
  2. customwas brought to room temperature at which it
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure
  4. customthe resulting residue was purified by DIAION (registered trademark) HP20 column chromatography (with elution by methanol)
  5. concentrationThe eluted fraction was concentrated under reduced pressure and to a solution of the resulting compound in water (2 mL)
  6. additionacetone (100 mL) was added
  7. stirringthe mixture was stirred at room temperature for an hour
  8. filtrationThe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-5f93ff3a24e14a77af374bd34be3b4a3
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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