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

HRID 718884Notes

Reaction equation

HRID 718884 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-ccbf37cd2bee4b238fddf90a8af2791f
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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