Hydrochloric Acid → HCID 117701563, compound

HRID 1507450Notes

Reaction equation

HRID 1507450 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH:19]=[O:20])=[C:17]2[C:12]([C:13](=[O:32])[C:14]([CH3:31])=[C:15]([CH:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:30])[CH2:28][CH3:29])[CH2:23][CH2:22]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.O.O.P([O-])(O)(O)=[O:41].[Na+].Cl([O-])=O.[Na+].Cl>O.C(O)(C)(C)C>[CH2:1]([O:8][C:9]1[C:18]([C:19]([OH:41])=[O:20])=[C:17]2[C:12]([C:13](=[O:32])[C:14]([CH3:31])=[C:15]([CH:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:30])[CH2:28][CH3:29])[CH2:23][CH2:22]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 117701716HCID 117701716, compound

Product 1

HCID 117701563HCID 117701563, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a mixture composed of 7-(benzyloxy)-3-methyl-4-oxo-2-(1-propanoylpiperidin-4-yl)-4H-chromene-8-carbaldehyde (400 mg, 0.92 mmol) obtained in Example 34-2, tert-butyl alcohol (8 mL), water (8 mL), 2-methyl-2-butene (8 mL), and sodium dihydrogen phosphate dihydrate (864 mg, 5.54 mmol), 80% sodium chlorite (313 mg, 2.77 mmol) was added under cooling with ice, and then the mixture was brought back to room temperature and stirred for 19 hours. A 0.2 N aqueous hydrochloric acid solution (20 mL) was added to the reaction solution, and then the organic solvent was distilled off under reduced pressure. The resulting solid was collected by filtration to obtain 407 mg of the title compound (yield: 95%).

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. customwas brought back to room temperature
  4. distillationthe organic solvent was distilled off under reduced pressure
  5. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-5f4ed039cece49dda8a6ab7604d0e85f
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

Loading…