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

HRID 43901Notes

Reaction equation

HRID 43901 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[CH:24]=[C:23](C(OCC)=O)[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-:30].[Li+].C1[CH2:36][O:35]CC1.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:36]([OH:35])=[O:30])=[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

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68406362Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-1,3-benzothiazole-6-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 83%

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-6-carboxylate obtained in Example (225d) (124 mg, 0.29 mmol) was dissolved in methanol (3 mL). A 2 N aqueous lithium hydroxide solution (1.43 mL, 2.86 mmol) was added, and the mixture was stirred at room temperature for 50 minutes. THF (1.5 mL) was added, followed by further stirring for three hours. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (2.5 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 96 mg of the title compound as a white solid (83%).

Workup

  1. stirringby further stirring for three hours
  2. washthe mixture was washed with ethyl acetate
  3. additionA 1 N aqueous hydrochloric acid solution (2.5 mL) was added to the aqueous layer
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washwashed in diethyl ether

Sources & evidence

ORD record
ord-1090c9e9bf5a4c88b0ea1897c62e151b
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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