Hydrochloric Acid → HCID 57405561, compound

HRID 632854Notes

Reaction equation

HRID 632854 reaction equation
[CH:1]1([N:4]2[C:12]3[CH:11]=[CH:10][N:9]=[CH:8][C:7]=3[N:6]([CH2:13][C:14]3[N:15]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:16]4[C:21]([C:22]=3[C:23]([O:25]CC)=[O:24])=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:5]2=[O:33])[CH2:3][CH2:2]1.[OH-].[Li+].Cl>C1COCC1.O>[CH:1]1([N:4]2[C:12]3[CH:11]=[CH:10][N:9]=[CH:8][C:7]=3[N:6]([CH2:13][C:14]3[N:15]([CH2:28][CH2:29][CH:30]([CH3:31])[CH3:32])[C:16]4[C:21]([C:22]=3[C:23]([OH:25])=[O:24])=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:5]2=[O:33])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57405395HCID 57405395, compound

Product 1

HCID 57405561HCID 57405561, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Compound 18 (0.5 g, 1 mmol) was dissolved in THF (25 mL), lithium hydroxide (48 mg, 2 mmol) dissolved in water (5 mL) was added. The resulting mixture was stirred at 60° C. overnight. The reaction mixture was allowed to cool down to room temperature then poured in water. The pH of the resulting mixture was adjusted to pH=4 by addition of a 1 M solution of hydrochloric acid. Then the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated. The residue was purified by column chromatography using dichloromethane and methanol. The title compound 17 (400 mg, 94%) was isolated as a white powder. m/z=419 (M+H)+.

Workup

  1. additionwas added
  2. temperatureto cool down to room temperature
  3. extractionThen the mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-631dcd9e116746738df40254f0abeb9e
Source dataset
uspto-grants-2016_04
Patent number
US09321768B2

Reaction notes

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