Sodium Hydroxide → HCID 15888085, compound

HRID 1108900Notes

Reaction equation

HRID 1108900 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]3[CH2:24][CH:23]([CH2:25][C:26]([O:28]CC)=[O:27])[C:22]4[CH:31]=[CH:32][CH:33]=[CH:34][C:21]=4[CH2:20][C:19]=3[CH:35]=2)[CH:5]=1>CCO>[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]3[CH2:24][CH:23]([CH2:25][C:26]([OH:28])=[O:27])[C:22]4[CH:31]=[CH:32][CH:33]=[CH:34][C:21]=4[CH2:20][C:19]=3[CH:35]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54315824HCID 54315824, compound

Product 1

HCID 15888085HCID 15888085, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 N NaOH (0.144 mL, 0.144 mmole) was added to a solution of ethyl (±)-10,11-dihydro-3-[3-(4-methyl-2-pyridylamino)-1-propyloxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (35 mg, 0.08 mmole) in EtOH(5 mL) at RT. The mixture was warmed overnight in an oil bath set at 32° C., then was concentrated. The residue was dissolved in H2O (3 mL), and the solution was acidified with 20% TFA. ODS chromatography (5-10% CH3CN/H2O containing 0.1% TFA) followed by concentration and lyophilization gave the title compound as a white powder: MS (ES) m/e 417.3(M+H)+. Anal. Calcd for C26H2N2O3 . 2.0 TFA . 1.0 H2O: C, 54.38; H,4.87; N, 4.23. Found: C, 54.66; H, 6.4.53; N, 4.32.

Workup

  1. temperatureThe mixture was warmed overnight in an oil bath
  2. customset at 32° C.
  3. concentrationwas concentrated
  4. dissolutionThe residue was dissolved in H2O (3 mL)
  5. concentrationODS chromatography (5-10% CH3CN/H2O containing 0.1% TFA) followed by concentration and lyophilization

Sources & evidence

ORD record
ord-73bdc1c829a945c1b9c72ae1c96fea19
Source dataset
uspto-grants-2000_05
Patent number
US06069158

Reaction notes

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