Hydrochloric Acid → HCID 117701692, compound

HRID 1507436Notes

Reaction equation

HRID 1507436 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:28])[C:7]([CH3:27])=[C:8]([C@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[CH2:18][CH2:19][O:20]C3CCCCO3)[O:9]2)=[CH:4][CH:3]=1.CO.[ClH:31]>O>[ClH:31].[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:28])[C:7]([CH3:27])=[C:8]([C@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[CH2:18][CH2:19][OH:20])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 117701726HCID 117701726, compound

Product 1

HCID 117701692HCID 117701692, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture composed of 7-hydroxy-3,8-dimethyl-2-{(2R)-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrrolidin-2-yl}-4H-chromen-4-one (77 mg, 0.20 mmol) obtained in Example 4-1, methanol (6 mL), concentrated hydrochloric acid (0.5 mL), and water (1 mL) was heated with stirring at a bath temperature of 55° C. for 20 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by reverse-phase HPLC. A 1 N aqueous hydrochloric acid solution (4 mL) was added to a fraction containing the compound of interest, and then the mixture was concentrated under reduced pressure. Diethyl ether and methanol were added to the obtained residue, and the mixture was powdered. The obtained solid was collected by filtration and then dried in a vacuum pump to obtain 40 mg of the title compound (yield: 53%).

Workup

  1. temperaturewas heated
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe obtained residue was purified by reverse-phase HPLC
  4. additionA 1 N aqueous hydrochloric acid solution (4 mL) was added to a fraction
  5. additioncontaining the compound of interest
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionDiethyl ether and methanol were added to the obtained residue
  8. filtrationThe obtained solid was collected by filtration
  9. customdried in a vacuum pump

Sources & evidence

ORD record
ord-e5eb196338654e2ab4e587dec52029ef
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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