Hydrochloric Acid → HCID 23143307, compound

HRID 732216Notes

Reaction equation

HRID 732216 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:31]=[C:32]([NH:36][CH2:37][CH3:38])[O:33][C:34]=2[CH3:35])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>CN(C)C=O.CO.O>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[N:31]=[C:32]([N:36]([CH2:2][C:3]3[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]4[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=4)=[CH:5][CH:4]=3)[CH2:37][CH3:38])[O:33][C:34]=2[CH3:35])=[CH:28][CH:29]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoateHCID 23143283HCID 23143283, compound

Product 1

HCID 23143307HCID 23143307, compoundYield 5.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-(4-{[4-(chloromethyl)benzyl]-oxy}phenyl)propanoate (50 mg, 0.16 mmol) in N,N-dimethylformamide (1 mL) were added a solution of 4-(4-chlorophenyl)-N-ethyl-5-methyl-1,3-oxazole-2-amine (45 mg, 0.19 mmol) in N,N-dimethylformamide (0.5 mL) and potassium carbonate (33 mg, 0.24 mmol), and the mixture was stirred at 70° C. for 66 hr. Water (2 mL) was added to the reaction mixture and the mixture was extracted with dichloromethane (2 mL). The organic layer was concentrated under reduced pressure with a centrifugal concentration apparatus (GeneVac). The obtained resultant product was dissolved in methanol (2 mL), 1N aqueous sodium hydroxide solution (0.32 mL, 0.32 mmol) was added, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with dichloromethane (2 mL). The organic layer was concentrated under reduced pressure with a centrifugal concentration apparatus (GeneVac). The residue was purified by preparative HPLC (gradient cycle B) to give the title compound (4.6 mg, yield 5%).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2 mL)
  2. concentrationThe organic layer was concentrated under reduced pressure with a centrifugal concentration apparatus (GeneVac)
  3. customThe obtained resultant product
  4. stirringthe mixture was stirred at room temperature for 18 hr
  5. extractionextracted with dichloromethane (2 mL)
  6. concentrationThe organic layer was concentrated under reduced pressure with a centrifugal concentration apparatus (GeneVac)
  7. customThe residue was purified by preparative HPLC (gradient cycle B)

Sources & evidence

ORD record
ord-6162249153604db1a8bf0d4cabc5ac38
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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