Sodium Hydroxide → HCID 11760895, compound

HRID 1369241Notes

Reaction equation

HRID 1369241 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]3[CH2:20][CH:19]([CH2:21][C:22]([O:24]CC)=[O:23])[C:18]4[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=4[CH2:16][C:15]=3[CH:31]=2)[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]3[CH2:20][CH:19]([CH2:21][C:22]([OH:24])=[O:23])[C:18]4[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=4[CH2:16][C:15]=3[CH:31]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12071475HCID 12071475, compound

Product 1

HCID 11760895HCID 11760895, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (±)-10,11-dihydro-3-[2-(6-aminopyridin-2-yl)-1-ethoxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (0.030 g, 0.072 mmole) and 1.0 N NaOH (0.14 mL, 0.14 mmole) in MeOH (2 mL) was stirred at RT overnight, then was concentrated. The residue was dissolved in H2O and the pH of the solution was adjusted to 7 with 1.0 N HCl. Concentration and chromatography on a C-18 Bond Elute column (10:9:1 CH3CN/H2O/TFA) gave the title compound (0.013 g): MS (ES) m/e 389 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in H2O
  3. concentrationConcentration and chromatography on a C-18 Bond
  4. washElute column (10:9:1 CH3CN/H2O/TFA)

Sources & evidence

ORD record
ord-bdb473e1f83c457092d32dc34053e0e1
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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