Sodium Hydroxide → HCID 15888086, compound

HRID 636312Notes

Reaction equation

HRID 636312 reaction equation
C([C:3]1[C:13]2[CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[C:10]3[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=3[CH2:8][C:7]=2[CH:6]=[C:5]([O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][CH2:32][CH3:33])[N:26]=2)[CH:4]=1)C.[OH-].[Na+]>CO>[CH2:32]([NH:31][C:27]1[N:26]=[C:25]([CH2:24][CH2:23][O:22][C:5]2[CH:4]=[CH:3][C:13]3[CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[C:10]4[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=4[CH2:8][C:7]=3[CH:6]=2)[CH:30]=[CH:29][CH:28]=1)[CH3:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86755426HCID 86755426, compound

Product 1

HCID 15888086HCID 15888086, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl (±)-10,11-dihydro-3-[2-[6-(ethylamino)-2-pyridyl]-1-ethoxy]-5H-dibenzo[a,d]cycloheptene-10-acetic acid (80 mg, 0.18 mmol) was dissolved in MeOH (3 mL), and 1.0 N NaOH (0.22 mL, 0.22 mmol) was added. The solution was stirred at RT overnight, then was concentrated in vacuum. The residue was dissolved in H2O (3 mL), and the solution was acidified with 20% TFA. Chromatography on C-18 Bond Elute (30% CH3CN/H2O containing 0.1% TFA) gave the title compound as a white solid: MS(ES) 417 (M+H)+. Anal. Calcd for C26H28N2O3.1.3 CF3CO2H: C, 60.83; H, 5.23; N, 4.96. Found: C, 60.64; H, 5.26; N, 4.26.

Workup

  1. concentrationwas concentrated in vacuum
  2. dissolutionThe residue was dissolved in H2O (3 mL)
  3. washChromatography on C-18 Bond Elute (30% CH3CN/H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-334fabd583da419db207df78ceedee38
Source dataset
uspto-grants-2001_02
Patent number
US06191304B1

Reaction notes

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