Water → HCID 57917618, compound

HRID 1878404Notes

Reaction equation

HRID 1878404 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:37])[C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:29])=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.[OH-].[Li+].O>CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:37])[C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:29])=[CH:23][CH:22]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57917641HCID 57917641, compound

Product 1

HCID 57917618HCID 57917618, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

Methyl 4-methoxy-3-((4-(4-(3-phenylureido)benzoyl)piperazin-1-yl)methyl)benzoate (216 mg, 0.43 mmol) was dissolved in methanol (20 mL) at room temperature. Lithium hydroxide (51.5 mg, 2.15 mmol) was added, followed by water (1 mL). The mixture was stirred at 45° C. overnight and concentrated under vacuum. The residue was dissolved in water (15 mL) and brought to pH ˜3 with 1M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate (×2) and with dichloromethane (×2). The combined organic phases were dried on magnesium sulfate, filtered and concentrated under vacuum. The residue was submitted to silica chromatography (0-10% methanol in dichloromethane as eluant) to give the title compound (78 mg). MS (ESI) m/z 489.1 [M+H]+

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in water (15 mL)
  3. extractionThe mixture was extracted with ethyl acetate (×2) and with dichloromethane (×2)
  4. customThe combined organic phases were dried on magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4eb595039dd348f58d41d462e122bd90
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

Loading…