Lithium hydroxide, monohydrate → 5-(4-Methoxyphenylcarbamoyl)-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid

HRID 1629787Notes

Reaction equation

HRID 1629787 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:32])[CH2:11][C:12]([NH:14][C:15]([CH3:31])([CH2:21][C:22](=O)[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[C:16]([O:18]CC)=[O:17])=[O:13])=[CH:5][CH:4]=1.O.[OH-].[Li+]>C1COCC1.O.CC(O)=O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([C:11]2[C:12](=[O:13])[NH:14][C:15]([CH3:31])([C:16]([OH:18])=[O:17])[CH2:21][C:22]=2[C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)=[O:32])=[CH:7][CH:8]=1

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86685878Ethyl 2-(3-(4-methoxyphenylamino)-3-oxopropanamido)-2-methyl-4-oxo-4-p-tolylbutanoate

Product 1

HCID 866858795-(4-Methoxyphenylcarbamoyl)-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylic acidYield 72%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 102C (0.033 g, 0.075 mmol) in THF (8 mL) and water (1.600 mL) was added lithium hydroxide monohydrate (3.77 mg, 0.090 mmol) and the reaction mixture was stirred at rt for 1 h. The reaction mixture was acidified with AcOH (5 drops) and diluted with EtOAc (10 mL) and water (3 mL). The phases were separated and the aqueous phase was extracted with EtOAc (10 mL). The organic phases were combined and dried over MgSO4, filtered, and concentrated in vacuo to give the desired product (0.0213 g, 72%) as a white solid. LCMS Anal. Calc'd for C22H22N2O5 394.15, found [M+H] 395.0.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0b99acf85cd42c3b21ef6442cd09050
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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