Lithium hydroxide, monohydrate → 2-(1-Allyl-2-(benzylcarbamoyl)hydrazinyl)acetic acid

HRID 1254482Notes

Reaction equation

HRID 1254482 reaction equation
[CH2:1]([N:4]([CH2:16][C:17]([O:19]CC)=[O:18])[NH:5][C:6](=[O:15])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:2]=[CH2:3].O.[OH-].[Li+]>O1CCCC1.CO.O.O>[CH2:1]([N:4]([CH2:16][C:17]([OH:19])=[O:18])[NH:5][C:6](=[O:15])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59541461Ethyl 2-(1-allyl-2-(benzylcarbamoyl)hydrazinyl)acetate

Product 1

HCID 594799102-(1-Allyl-2-(benzylcarbamoyl)hydrazinyl)acetic acidYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To the solution of ethyl 2-(1-allyl-2-(benzylcarbamoyl)hydrazinyl)acetate (Compound V-1) 1.31 g (4.5 mmol) in tetrahydrofuran/methanol/water (2:3:1) 24 ml, lithium hydroxide monohydrate 377 mg (9.0 mmol) was added and stirred at room temperature for 5 hour. 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 then filtered. The filtrate was concentrated in vacuo to obtain the title compound 982 mg (83%).

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. filtrationthen filtered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-df27082e4ea14ef69bf56d7955b83e16
Source dataset
uspto-grants-2013_06
Patent number
US08455488B2

Reaction notes

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