Sodium Hydroxide → HCID 66759166, compound

HRID 556996Notes

Reaction equation

HRID 556996 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:41])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:23]4[CH:24]=[CH:25][CH:26]=[N:27][C:22]=4[CH2:21][O:20][C:19]4[CH:28]=[CH:29][C:30]([O:32][CH2:33][CH2:34][O:35]C(=O)C)=[CH:31][C:18]3=4)[CH2:10][C:9]2([CH3:40])[CH3:39])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:41])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:23]4[CH:24]=[CH:25][CH:26]=[N:27][C:22]=4[CH2:21][O:20][C:19]4[CH:28]=[CH:29][C:30]([O:32][CH2:33][CH2:34][OH:35])=[CH:31][C:18]3=4)[CH2:10][C:9]2([CH3:39])[CH3:40])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66758364HCID 66758364, compound

Product 1

HCID 66759166HCID 66759166, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 75.8 mg (0.1314 mmol) Acetic acid 2-(5-{3-[4-(4-chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidin-1-yl]-propylidene}-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yloxy)-ethyl ester (example 10) in ethanol (5 ml) was added a 15% sodium hydroxide in water (2 ml) solution. The reaction was heated to reflux for 30 minutes, at which time the LC/MS showed it to be complete. After cooling to room temperature the reaction was worked up by diluting with ethyl acetate and washing with water and brine. The combined aqueous layers were back extracted with ethyl acetate. The combined organics were dried over magnesium sulfate and the solvent was distilled under reduced pressure. The residue was purified by reverse phase HPLC to give the title compound (42 mg, 60%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 30 minutes, at which time the LC/MS
  3. washwashing with water and brine
  4. extractionThe combined aqueous layers were back extracted with ethyl acetate
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. distillationthe solvent was distilled under reduced pressure
  7. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-0cbac26bbb234d8694b18a908aca7985
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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