Acetic Acid → HCID 89583168, compound

HRID 402842Notes

Reaction equation

HRID 402842 reaction equation
[CH3:1][C:2]1[C:3]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[C:4]([CH3:30])[CH:5]=[C:6]([CH2:8][N:9]2[CH2:29][CH2:28][C:12]3([O:16][C:15](=[O:17])[N:14]([C:18]4[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=4)[CH2:13]3)[CH2:11][CH2:10]2)[CH:7]=1.[OH-].[K+].C(O)(=O)C>C(O)C>[CH3:1][C:2]1[C:3]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[C:4]([CH3:30])[CH:5]=[C:6]([CH2:8][N:9]2[CH2:29][CH2:28][C:12]3([O:16][C:15](=[O:17])[N:14]([C:18]4[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=4)[CH2:13]3)[CH2:11][CH2:10]2)[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 89583175HCID 89583175, compound

Product 1

HCID 89583168HCID 89583168, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of half of the crude methyl 4-{8-[(4′-fluoro-2,6-dimethylbiphen-4-yl)methyl]-2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl}benzoate from Step 3 (˜0.065 mmol) in ethanol (1 mL) was added excess aqueous potassium hydroxide and the reaction was stirred at room temperature for 24 hours. The mixture was then acidified with acetic acid and the title product (5.4 mg) was isolated by mass directed reverse phase (C18) chromatography (0.1% ammonium hydroxide) and evaporation of the product fractions.

Sources & evidence

ORD record
ord-cee3111aeb8d4e45b7b439ad1a1dacb9
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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