Water → HCID 60135949, compound
Reaction equation
[OH-].[Li+].[Cl:3][C:4]1[N:5]=[C:6]([C:11]([NH:13][CH:14]2[CH2:17][N:16]([C:18]3[S:19][C:20]([C:26]([O:28]CC)=[O:27])=[C:21]([CH:23]([CH3:25])[CH3:24])[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]([NH:13][CH:14]2[CH2:17][N:16]([C:18]3[S:19][C:20]([C:26]([OH:28])=[O:27])=[C:21]([CH:23]([CH3:24])[CH3:25])[N:22]=3)[CH2:15]2)=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A 2 N aqueous lithium hydroxide solution (0.72 mL, 1.43 mmol) was added to a mixed solution of ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate obtained in Example (221c) (61 mg, 0.14 mmol) in methanol/THF (1.5 mL/1 mL) at room temperature, and the mixture was stirred at 40° C. for 70 minutes. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (1 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 45 mg of the title compound as a white solid (79%).
Workup
- washthe mixture was washed with ethyl acetate
- additionA 1 N aqueous hydrochloric acid solution (1 mL) was added to the aqueous layer
- extractionfollowed by extraction with ethyl acetate
- dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- washwashed in diethyl ether
Sources & evidence
- ORD record
- ord-ac3e5b5ea225447e9dc0899f8885ac1d
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927588B2
Reaction notes
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