Hydrochloric Acid → HCID 44226453, compound

HRID 1947134Notes

Reaction equation

HRID 1947134 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[N:29]([CH3:30])[C:28]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[N:21]([CH2:31][C:32](=[O:39])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:20](=[O:40])[C:19]=3[C:18]=2[O:41][CH3:42])=[O:16])[CH2:10][CH2:9]1)=[O:7])(=O)C.[OH-].[Na+].C(O)C.Cl>C1COCC1.O>[OH:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[N:29]([CH3:30])[C:28]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[N:21]([CH2:31][C:32](=[O:39])[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:20](=[O:40])[C:19]=3[C:18]=2[O:41][CH3:42])=[O:16])[CH2:10][CH2:9]1)=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 57860625HCID 57860625, compound

Product 1

HCID 44226453HCID 44226453, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of the compound of Example 123 (125 mg, 0.218 mmol) and 8N aqueous sodium hydroxide solution (1 mL) in THF (2 mL)-ethanol (7 mL) was stirred at room temperature for 2 hr. The reaction mixture was diluted with water, acidified with 6N hydrochloric acid (1.5 mL), and extracted twice with ethyl acetate. The extract was combined, washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate), and the obtained solid was recrystallized from ethyl acetate-THF to give the title compound (59.2 mg, 51%) as white crystals.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate)
  6. customthe obtained solid was recrystallized from ethyl acetate-THF

Sources & evidence

ORD record
ord-71cdf013b76c4a8097b5851d2abd5774
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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