Water → HCID 60135938, compound

HRID 43906Notes

Reaction equation

HRID 43906 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[N:5]=[C:6]([C:11]([N:13]([CH2:29][CH2:30][CH3:31])[CH:14]2[CH2:17][N:16]([C:18]3[S:19][C:20]([C:24]([O:26]CC)=[O:25])=[C:21]([CH3:23])[N:22]=3)[CH2:15]2)=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10].O>CO.C1COCC1>[Cl:3][C:4]1[N:5]=[C:6]([C:11]([N:13]([CH2:29][CH2:30][CH3:31])[CH:14]2[CH2:15][N:16]([C:18]3[S:19][C:20]([C:24]([OH:26])=[O:25])=[C:21]([CH3:23])[N:22]=3)[CH2:17]2)=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67548625ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](n-propyl)amino}azetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 60135938HCID 60135938, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 2 N aqueous lithium hydroxide solution (1.30 mL, 2.59 mmol) was added to a mixed solution of ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](n-propyl)amino}azetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (227d) (114 mg, 0.26 mmol) in methanol/THF (3 mL/0.5 mL), and the mixture was stirred at room temperature for 16 hours. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (4.5 mL) was added to the aqueous layer, followed by extraction with ethyl acetate. 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 58 mg of the title compound as a white solid (54%).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. additionA 1 N aqueous hydrochloric acid solution (4.5 mL) was added to the aqueous layer
  3. extractionfollowed by extraction with ethyl acetate
  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-4daf5cf56b1941d5bb3a7b8698542579
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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