Lithium hydroxide, monohydrate → 2-(2-(Benzylcarbamoyl)-1-methylhydrazinyl)acetic acid

HRID 576877Notes

Reaction equation

HRID 576877 reaction equation
[CH3:1][N:2]([CH2:14][C:15]([O:17]CC)=[O:16])[NH:3][C:4](=[O:13])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Li+]>O1CCCC1.CO.O.O>[CH2:6]([NH:5][C:4]([NH:3][N:2]([CH2:14][C:15]([OH:17])=[O:16])[CH3:1])=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66977957ethyl 2-(1-Methyl-2-(benzylcarbamoyl)hydrazinyl)acetate

Product 1

HCID 533974892-(2-(Benzylcarbamoyl)-1-methylhydrazinyl)acetic acidYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 2-(1-methyl-2-(benzylcarbamoyl)hydrazinyl)acetate (Compound XXXII-1) 1.33 g (5.0 mmol) in tetrahydrofuran/methanol/water (2:3:1) 24 ml, lithium hydroxide monohydrate 420 mg (10.0 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water 25 ml and washed with ether 25 ml. The aqueous phase was acidified with 10%-citric acid 25 ml and extracted with chloroform 30 ml. The organic phase was washed with brine 25 ml and dried with magnesium sulfate and then filtered. The filtrate was concentrated in vacuo to obtain the title compound 1.05 g (88%).

Workup

  1. washwashed with ether 25 ml
  2. extractionextracted with chloroform 30 ml
  3. washThe organic phase was washed with brine 25 ml
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-44dbb38d3e9c442083f9b24f2ebb3a23
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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