Water → HCID 66588376, compound

HRID 1469149Notes

Reaction equation

HRID 1469149 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]2[CH2:15][CH2:16][N:17]([C:19](=[O:32])[CH2:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[C:23]([OH:31])[CH:22]=3)[CH2:18][C:7]1=2.[OH-].[Na+].O>COC.CO>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]2[CH2:15][CH2:16][N:17]([C:19](=[O:32])[CH2:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[C:23]([OH:31])[CH:22]=3)[CH2:18][C:7]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66587919HCID 66587919, compound

Product 1

HCID 66588376HCID 66588376, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 20484492HCID 20484492, compoundSolvent

Procedure

To 3.0 mL of a solution of the compound (53.8 mg) produced in Example 64 in dimethyl ether/methanol (1:1) was added a 1N aqueous sodium hydroxide solution (1.5 mL), the mixture was stirred at room temperature for 2.5 hours, and at 50° C. for 3 hours, and allowed to stand at room temperature overnight. On the next day, the resultant was stirred again at 50° C. for 5 hours, and water was added to the reaction solution. After washed with tert-butyl methyl ether, 1N hydrochloric acid was added to the aqueous layer to make the solution acidic (pH 3), and the resultant was extracted two times using ethyl acetate. The extracted organic layer was washed with an aqueous saturated sodium chloride solution, and dried with anhydrous magnesium sulfate, and the solution obtained by filter filtration was concentrated under reduced pressure to obtain the title compound (46.6 mg) having the following physical property values.

Workup

  1. waitat 50° C. for 3 hours
  2. waitto stand at room temperature overnight
  3. stirringOn the next day, the resultant was stirred again at 50° C. for 5 hours
  4. washAfter washed with tert-butyl methyl ether, 1N hydrochloric acid
  5. additionwas added to the aqueous layer
  6. extractionthe resultant was extracted two times
  7. washThe extracted organic layer was washed with an aqueous saturated sodium chloride solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customthe solution obtained
  10. filtrationby filter
  11. filtrationfiltration
  12. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-82dbfc3c15194f58bc061c36deeb295d
Source dataset
uspto-grants-2015_04
Patent number
US09006246B2

Reaction notes

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