Hydrochloric Acid → HCID 56943751, compound

HRID 2387735Notes

Reaction equation

HRID 2387735 reaction equation
Cl.[CH3:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([O:10][CH2:11][C@@:12]2([C:25]3[CH:30]=[CH:29][C:28]([O:31]COC)=[C:27]([F:35])[CH:26]=3)[CH2:14][C@H:13]2[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=2)=[O:16])=[CH:5][N:4]=1.[OH-].[Na+]>C1COCC1>[CH3:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([O:10][CH2:11][C@@:12]2([C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([F:35])[CH:26]=3)[CH2:14][C@H:13]2[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=2)=[O:16])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67282950HCID 67282950, compound

Product 1

HCID 56943751HCID 56943751, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 N hydrochloric acid (15 ml) was added to a THF (15 ml) solution of the compound 321-9 (1.01 g), and the obtained mixture was stirred at room temperature for 2 hours. A 5 N sodium hydroxide aqueous solution was added to the reaction solution under cooling on ice for neutralization, and the mixture was then extracted with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride aqueous solution, then dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration, so as to obtain the title compound 321 (721 mg).

Workup

  1. temperatureunder cooling on ice for neutralization
  2. extractionthe mixture was then extracted with ethyl acetate
  3. washThe obtained organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe obtained residue was washed with ethyl acetate
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-439b630226564e9e8d64d568b0c0d99d
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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