Hydrochloric Acid → HCID 117701682, compound

HRID 1507434Notes

Reaction equation

HRID 1507434 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[C:20]([CH3:21])=[C:19]2[C:14]([C:15](=[O:30])[C:16]([CH3:29])=[C:17]([C@H:22]3[CH2:26][CH2:25][CH2:24][N:23]3[CH2:27][CH3:28])[O:18]2)=[CH:13][CH:12]=1)(=O)C.Cl>CO>[CH2:27]([N:23]1[CH2:24][CH2:25][CH2:26][C@@H:22]1[C:17]1[O:18][C:19]2[C:14]([C:15](=[O:30])[C:16]=1[CH3:29])=[CH:13][CH:12]=[C:11]([OH:10])[C:20]=2[CH3:21])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 117701588HCID 117701588, compound

Product 1

HCID 117701682HCID 117701682, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (97 mg, 0.70 mmol) was added to a solution of 2-[(2R)-1-ethylpyrrolidin-2-yl]-3,8-dimethyl-4-oxo-4H-chromen-7-yl acetate (58 mg, 0.18 mmol) obtained in Example 3-1 in methanol (4 mL), and then the mixture was stirred at room temperature for 2 hours. A 1 N aqueous hydrochloric acid solution (2 mL) was added dropwise thereto, and then methanol in the reaction solution was distilled off under reduced pressure. Water (2 mL) was added to the residue, and then the pH of the mixture was adjusted to around 8 by the dropwise addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. Ethyl acetate and n-hexane were added to the obtained residue, and the mixture was powdered to obtain 40 mg of the title compound (yield: 79%).

Workup

  1. distillationmethanol in the reaction solution was distilled off under reduced pressure
  2. additionWater (2 mL) was added to the residue
  3. additionthe pH of the mixture was adjusted to around 8 by the dropwise addition of a saturated aqueous solution of sodium bicarbonate
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationThe desiccant was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionEthyl acetate and n-hexane were added to the obtained residue

Sources & evidence

ORD record
ord-8a6719c74f8b4f14bdf0fd9c5f3c09fc
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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