Water → 2-(3-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-benzothiazole-7-carboxylic acid

HRID 43897Notes

Reaction equation

HRID 43897 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[S:17][C:18]4[C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[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[S:17][C:18]4[C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH2:13]2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67548592Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-benzothiazole-7-carboxylate

Product 1

HCID 601358622-(3-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-benzothiazole-7-carboxylic acidYield 58.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-benzothiazole-7-carboxylate obtained in Example (224c) (350 mg, 0.81 mmol) was dissolved in methanol (8 mL). A 2 N aqueous lithium hydroxide solution (4.03 mL, 8.07 mmol) was added, and the mixture was stirred at room temperature for 18 hours. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (8 mL) was added to the aqueous layer, and then the solvent was evaporated under reduced pressure. The resulting residue was suspended and washed in methanol. Following filtration, the resulting solid was washed with water to obtain 191 mg of the title compound as a white solid (58%).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. additionA 1 N aqueous hydrochloric acid solution (8 mL) was added to the aqueous layer
  3. customthe solvent was evaporated under reduced pressure
  4. washwashed in methanol
  5. filtrationfiltration
  6. washthe resulting solid was washed with water

Sources & evidence

ORD record
ord-8a821a090cb24119b5e27afe52a784a2
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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