Hydrochloric Acid → HCID 67211009, compound

HRID 452143Notes

Reaction equation

HRID 452143 reaction equation
[C:1]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]([CH2:15][C:16]2[CH:33]=[CH:32][C:19]3/[C:20](=[CH:29]/[C:30]#[N:31])/[C:21]4[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=4[CH2:23][CH2:24][C:18]=3[CH:17]=2)[C:8](=[O:14])[CH2:9][C:10]([O:12]C)=[O:11])[CH:2]=1.[OH-].[Na+].Cl>C(O)C>[C:1]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]([CH2:15][C:16]2[CH:33]=[CH:32][C:19]3/[C:20](=[CH:29]/[C:30]#[N:31])/[C:21]4[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=4[CH2:23][CH2:24][C:18]=3[CH:17]=2)[C:8](=[O:14])[CH2:9][C:10]([OH:12])=[O:11])[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67211214HCID 67211214, compound

Product 1

HCID 67211009HCID 67211009, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[step 2] (E)-[2-(N-(Biphenyl-3-yl)-3-methoxy-3-oxopropanamido)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (52 mg, 0.10 mmol) obtained in step 1 was dissolved in ethanol (2 mL), 2 mol/L aqueous sodium hydroxide solution (0.1 mL) was added, and the mixture was stirred at room temperature for 3 hr. The mixture was adjusted to pH 2 with 2 mol/L hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by reversed-phase liquid chromatography (water/acetonitrile=7/3 to 1/9) to give the title compound (compound 44) (30 mg, 60%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reversed-phase liquid chromatography (water/acetonitrile=7/3 to 1/9)

Sources & evidence

ORD record
ord-21da98947b7a4f6f8f8d3c7c0d092ecf
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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