Water → HCID 60135935, compound

HRID 43879Notes

Reaction equation

HRID 43879 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]([C:22]([O:24]CC)=[O:23])=[C:19]([CH3:21])[N:20]=3)[CH2:13]2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+].C1COCC1.O>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][CH:12]2[CH2:13][N:14]([C:16]3[S:17][C:18]([C:22]([OH:24])=[O:23])=[C:19]([CH3:21])[N:20]=3)[CH2:15]2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68405881HCID 68405881, compound

Product 1

HCID 60135935HCID 60135935, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (218c) (145 mg, 0.36 mmol) was dissolved in methanol (3.6 mL). A 2 N aqueous lithium hydroxide solution (1.82 mL, 3.64 mmol) was added, and the mixture was stirred at room temperature for 27 hours. THF (2 mL) was added, followed by further stirring for 22 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 mL) 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 123 mg of the title compound as a white solid (91%).

Workup

  1. stirringby further stirring for 22 hours
  2. washthe mixture was washed with ethyl acetate
  3. additionA 1 N aqueous hydrochloric acid solution (4 mL) was added to the aqueous layer
  4. extractionfollowed by extraction with a chloroform/methanol mixed solvent
  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-d6c240c35f494309b3f04d1880808d7e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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