Lithium Hydroxide → HCID 57495635, compound

HRID 1092355Notes

Reaction equation

HRID 1092355 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][C:14]3([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[N:13]([CH:22]3[CH2:24][CH2:23]3)[C:12]2=[O:25])=[CH:7][CH:6]=1)C.[Li+].[OH-]>C1COCC1.CO.CCOC(C)=O>[CH:22]1([N:13]2[C:14]3([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:15][N:11]([C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:26])=[O:3])=[CH:6][CH:7]=3)[C:12]2=[O:25])[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57495634HCID 57495634, compound

Product 1

HCID 57495635HCID 57495635, compoundYield 9.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 76 mg (2.1 mmol) 4-(1-Cyclopropyl-2-oxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzoic acid ethyl ester in 2 ml THF/Methanol 1.1 was treated with 0.5 ml of 1N LiOH. After stirring for 3 h the reaction mixture was acidified with 1N HCL, taken up in EtOAc and washed with water to give 65.5 mg of pure 4-(1-cyclopropyl-2-oxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzoic acid MS (API): 327.5 (M−H). A solution of 47 mg (1.3 mmol) 4-(1-cyclopropyl-2-oxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzoic acid and 27 mg (0.16 mmol) of 1,1-carbonyl diimidazole in 1 ml of THF was stirred under reflux for 1 h, then 32 mg (0.4 mmol) of Ammonium acetate was added and the stirring under reflux was continued for another 2 h. The reaction mixture was taken up in EtOAc and washed with 1N HCL and water. The crude product was crystallized in Ether/Heptan to give 25 mg of pure 4-(1-Cyclopropyl-2-oxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzamide. MS (ESI): 328.4 (MH+).

Workup

  1. washwashed with water

Sources & evidence

ORD record
ord-173582a4a3d0477982375c1791427933
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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