Water → HCID 60135964, compound

HRID 43889Notes

Reaction equation

HRID 43889 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:23]([O:25]C)=[O:24])=[C:19]([CH2:21][CH3:22])[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[CH2:13][N:14]([C:16]3[S:17][C:18]([C:23]([OH:25])=[O:24])=[C:19]([CH2:21][CH3:22])[N:20]=3)[CH2:15]2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67548482Methyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-ethyl-1,3-thiazole-5-carboxylate

Product 1

HCID 60135964HCID 60135964, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-ethyl-1,3-thiazole-5-carboxylate obtained in Example (222c) (143 mg, 0.36 mmol) was dissolved in methanol (3.6 mL). A 2 N aqueous lithium hydroxide solution (1.80 mL, 3.59 mmol) was added, and the mixture was stirred at room temperature for 18.5 hours. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (3 mL) was added to the aqueous layer. The precipitated solid was collected by filtration to obtain 46 mg of the title compound as a white solid (33%).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. additionA 1 N aqueous hydrochloric acid solution (3 mL) was added to the aqueous layer
  3. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-5d5ec0b2d82c4ecf8bb7523cbeeec5f9
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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