Water → HCID 59615426, compound

HRID 43881Notes

Reaction equation

HRID 43881 reaction equation
[OH-].[Li+].[CH2:3]([C:7]1[N:8]=[C:9]([N:15]2[CH2:18][CH:17]([NH:19][C:20]([C:22]3[NH:23][C:24]([CH2:28][CH3:29])=[C:25]([Cl:27])[N:26]=3)=[O:21])[CH2:16]2)[S:10][C:11]=1[C:12]([OH:14])=[O:13])[CH2:4][CH2:5]C.O>CO.C1COCC1>[Cl:27][C:25]1[N:26]=[C:22]([C:20]([NH:19][CH:17]2[CH2:16][N:15]([C:9]3[S:10][C:11]([C:12]([OH:14])=[O:13])=[C:7]([CH2:3][CH2:4][CH3:5])[N:8]=3)[CH2:18]2)=[O:21])[NH:23][C:24]=1[CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 60135957HCID 60135957, compound

Product 1

HCID 59615426HCID 59615426, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 2 N aqueous lithium hydroxide solution (1.53 mL, 3.07 mmol) was added to a mixed solution of ethyl 4-n-butyl-2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl)]amino}azetidin-1-yl-1,3-thiazole-5-carboxylate obtained in Example (220d) (214 mg, 0.50 mmol) in methanol/THF (3 mL/0.5 mL) at room temperature, followed by stirring for 18 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. The precipitated solid was collected by filtration to obtain 72 mg of the title compound as a white solid (57%).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. additionA 1 N aqueous hydrochloric acid solution (2.5 mL) was added to the aqueous layer
  3. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-beabef437785415fbe6e59c2f8f12fb2
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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