Dichloromethane → HCID 67372107, compound

HRID 1727102Notes

Reaction equation

HRID 1727102 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([CH2:18][S:19]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=3)=[O:20])([OH:17])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].O1CCCC1.C[Si](C)(C)[O-].[K+].[Cl:42]CCl>>[ClH:42].[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][C:14]([CH2:18][S:19]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:29][CH:30]=3)=[O:20])([OH:17])[CH2:15][CH2:16]2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 23085071HCID 23085071, compoundHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 67372107HCID 67372107, compound

Procedure

To a solution of the compound (150 mg) obtained in Example 44 in a mixture of anhydrous tetrahydrofuran (8 mL) and anhydrous dichloromethane (8 mL) was added 90% potassium trimethylsilanolate (125 mg) at room temperature, followed by stirring at the same temperature under nitrogen atmosphere for four hours. Insoluble matter was collected by filtration, was washed with dichloromethane and was dried. The insoluble matter was dissolved in water (1 mL) and was then treated with 1 N hydrochloric acid to adjust the pH of the mixture to 5 to 5.6. The precipitate was collected by filtration, washed with water and dried. The precipitate was suspended in methanol, and mixed with 10% solution of hydrogen chloride in methanol, then the mixture was stirred at room temperature, and the solvent was removed under reduced pressure. The residue was suspended in acetonitrile, washed at 40 to 50° C. with stirring for one hour, was collected by filtration, and dried under reduced pressure to yield the titled compound (58 mg) as crystals.

Workup

  1. filtrationInsoluble matter was collected by filtration
  2. washwas washed with dichloromethane
  3. customwas dried
  4. dissolutionThe insoluble matter was dissolved in water (1 mL)
  5. additionwas then treated with 1 N hydrochloric acid
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customdried
  9. additionmixed with 10% solution of hydrogen chloride in methanol
  10. stirringthe mixture was stirred at room temperature
  11. customthe solvent was removed under reduced pressure
  12. washwashed at 40 to 50° C.
  13. stirringwith stirring for one hour
  14. filtrationwas collected by filtration
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-a90321beb81d462f8a543b5b9f10910b
Source dataset
uspto-grants-2009_02
Patent number
US07494987B2

Reaction notes

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