Sodium Hydroxide → HCID 66758017, compound

HRID 242610Notes

Reaction equation

HRID 242610 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][O:5][C:6]1[CH:39]=[CH:38][C:9]2[O:10][CH2:11][C:12]3[N:37]=[CH:36][CH:35]=[CH:34][C:13]=3[C:14](=[CH:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][C:21]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)([OH:24])[C:20]([CH3:33])([CH3:32])[CH2:19]3)[C:8]=2[CH:7]=1.[OH-].[Na+]>CO.O>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:21]2([OH:24])[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH:15]=[C:14]3[C:13]4[CH:34]=[CH:35][CH:36]=[N:37][C:12]=4[CH2:11][O:10][C:9]4[CH:38]=[CH:39][C:6]([O:5][CH2:4][C:3]([OH:40])=[O:2])=[CH:7][C:8]3=4)[CH2:19][C:20]2([CH3:32])[CH3:33])=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66757650HCID 66757650, compound

Product 1

HCID 66758017HCID 66758017, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(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)-acetic acid methyl ester (0.060 g, 0.107 mmol) was dissolved in methanol (1.5 mL). Sodium hydroxide (150 uL, 1N stock solution) was added and the resulting mixture was stirred at room temperature. After stirring overnight at room temperature, the reaction mixture was concentrated in vacuo to give a yellow oil. The oil was suspended in water (2 mL) and then washed with ethyl acetate (3×3 mL). The aqueous layer was then acidified to pH=2 and extracted with ethyl acetate (3×5 mL). The pooled organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford a white solid (55 mg, 94%).

Workup

  1. stirringAfter stirring overnight at room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customto give a yellow oil
  4. washwashed with ethyl acetate (3×3 mL)
  5. extractionextracted with ethyl acetate (3×5 mL)
  6. dry with materialThe pooled organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bd0a707d2464ed0af2d45faee46ab2e
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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