Water → HCID 60135938, compound

HRID 1425374Notes

Reaction equation

HRID 1425374 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[N:5]=[C:6]([C:11]([N:13]([CH2:29][CH2:30][CH3:31])[CH:14]2[CH2:17][N:16]([C:18]3[S:19][C:20]([C:24]([O:26]CC)=[O:25])=[C:21]([CH3:23])[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]([N:13]([CH2:29][CH2:30][CH3:31])[CH:14]2[CH2:15][N:16]([C:18]3[S:19][C:20]([C:24]([OH:26])=[O:25])=[C:21]([CH3:23])[N:22]=3)[CH2:17]2)=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67548625ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](n-propyl)amino}azetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 60135938HCID 60135938, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 2 N aqueous lithium hydroxide solution (1.30 mL, 2.59 mmol) was added to a mixed solution of ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](n-propyl)amino}azetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (227d) (114 mg, 0.26 mmol) in methanol/THF (3 mL/0.5 mL), and the mixture was stirred at room temperature for 16 hours. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (4.5 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 58 mg of the title compound as a white solid (54%).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. additionA 1 N aqueous hydrochloric acid solution (4.5 mL) was added to the aqueous layer
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washwashed in diethyl ether

Sources & evidence

ORD record
ord-764d405348374be683ca43ee0e5e0afa
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

Loading…