Sodium Hydroxide → HCID 89823605, compound

HRID 1400072Notes

Reaction equation

HRID 1400072 reaction equation
Cl.NO.[OH-].[Na+].CC1[N:8]([C@H:13]2[CH2:20][C@@:19]3([C:21]([O:23][CH3:24])=[O:22])[C@H:15]([CH2:16][CH2:17][CH2:18]3)[CH2:14]2)C(C)=CC=1>O.CO>[NH2:8][C@H:13]1[CH2:20][C@@:19]2([C:21]([O:23][CH3:24])=[O:22])[C@H:15]([CH2:16][CH2:17][CH2:18]2)[CH2:14]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 71226046HCID 71226046, compound

Product 1

HCID 89823605HCID 89823605, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

To an aqueous solution of hydroxylamine hydrochloride (458 g, 6.59 mol) and sodium hydroxide (120 g, 3 mol) in water (350 mL) was added a solution of Example 1D (119 g, 0.454 mol) in methanol (2 L) and the mixture was stirred at 65° C. for 8 hours. The mixture was cooled to room temperature, sufficient water was added and the methanol was removed under reduced pressure. The resulting slurry was adjusted to pH 10 with an aqueous sodium hydroxide solution (2.5 N) and the reaction mixture was extracted with dichloromethane. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the title compound, which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe methanol was removed under reduced pressure
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-df50190fa9d44b46ab5ffdcb164f412a
Source dataset
uspto-grants-2014_12
Patent number
US08906911B2

Reaction notes

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