Water → HCID 60135886, compound

HRID 1425361Notes

Reaction equation

HRID 1425361 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][CH:12]2[CH2:15][N:14]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([O:21]CC)=[O:20])[CH2:13]2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+].O>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][CH:12]2[CH2:15][N:14]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([OH:21])=[O:20])[CH2:13]2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67548671Ethyl 3-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)benzoate

Product 1

HCID 60135886HCID 60135886, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)benzoate obtained in Example (223c) (84 mg, 0.22 mmol) was dissolved in methanol (2 mL). A 2 N aqueous lithium hydroxide solution (1.11 mL, 2.23 mmol) was added, and the mixture was stirred at room temperature for 20 hours. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution was added to the aqueous layer, followed by extraction with a chloroform/methanol mixed solvent. The combined organic layers were dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting solid was suspended and washed in diethyl ether to obtain 10 mg of the title compound as a white solid (13%).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. additionA 1 N aqueous hydrochloric acid solution was added to the aqueous layer
  3. extractionfollowed by extraction with a chloroform/methanol mixed solvent
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washwashed in diethyl ether

Sources & evidence

ORD record
ord-5c5b534727794dd2bae16789c19ccc8f
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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