Hydrochloric Acid → HCID 68772873, compound

HRID 2191086Notes

Reaction equation

HRID 2191086 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:36])[CH2:34][C:8]2[C:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([C:30]([O:32]C)=[O:31])[CH:25]=4)[CH:19]=3)=[C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:11][C:7]=2[C:6](=[O:35])[CH2:5]1.Cl>CCO.O>[CH3:3][C:4]1([CH3:36])[CH2:34][C:8]2[C:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([C:30]([OH:32])=[O:31])[CH:25]=4)[CH:19]=3)=[C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:11][C:7]=2[C:6](=[O:35])[CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68775509HCID 68775509, compound

Product 1

HCID 68772873HCID 68772873, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Sodium hydroxide (11 mg, 0.27 mmol) was added to a mixture of Example 215 (65 mg, 0.14 mmol) in EtOH (5 mL) and water (1 mL) and the reaction mixture was stirred at room temperature for 2 h. Water (5 mL) was added; the reaction mixture was adjusted to pH 6 with 1N aqueous hydrochloric acid and then extracted with EtOAc (2×15 mL). The combined organic layers were dried (magnesium sulfate) and the solvent was removed in vacuo to give the title compound (60 mg, 92%) as a yellow solid. δH (CDCl3) 8.91-8.78 (3H, m), 8.37 (1H, d, J 4.3 Hz), 8.04 (1H, s), 7.43 (1H, d, J 4.9 Hz), 3.74-3.62 (4H, m), 3.09-2.97 (4H, m), 2.54 (2H, s), 2.48 (2H, s), 1.06 (6H, s). LCMS (ES+) 464.0 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×15 mL)
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f963c695f83b49feb7200805a97a6687
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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