Sodium Hydroxide → HCID 131732142, compound

HRID 1400078Notes

Reaction equation

HRID 1400078 reaction equation
NO.Cl.[OH-].[Na+].CC1[N:8]([C@H:13]2[CH2:20][C@@:19]3([C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[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][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:22])[C@H:15]([CH2:16][CH2:17][CH2:18]2)[CH2:14]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 131732143HCID 131732143, compound

Product 1

HCID 131732142HCID 131732142, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

To a aqueous solution of NH2OH.HCl (8.4 g, 121.2 mmol) and NaOH (2.2 g, 19.54 mmol) in H2O (20 mL) was added a solution of Example 48C (2.81 g, 8.36 mmol) in MeOH (70 mL) and the mixture was heated at 65° C. for 8 hours. The mixture was cooled to room temperature, sufficient water was added and MeOH was removed under reduced pressure. The resulting slurry was adjusted to pH=10 with NaOH solution (2.5 N) and extracted with dichloromethane. The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated to give a crude product, which was purified by column chromatography (SiO2, dichloromethane:MeOH from 100:1 to 10:1) to get the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customMeOH was removed under reduced pressure
  3. extractionextracted with dichloromethane
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude product, which
  9. customwas purified by column chromatography (SiO2, dichloromethane:MeOH from 100:1 to 10:1)

Sources & evidence

ORD record
ord-08a65a1261474907988c5d5c461e5fb4
Source dataset
uspto-grants-2014_12
Patent number
US08906911B2

Reaction notes

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