Lithium hydroxide, monohydrate → HCID 67304006, compound

HRID 2361948Notes

Reaction equation

HRID 2361948 reaction equation
[CH2:1]([N:4]([C:16]([CH3:23])([CH3:22])[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]([C:16]([CH3:23])([CH3:22])[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 67304487HCID 67304487, compound

Product 1

HCID 67304006HCID 67304006, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 2-(1-allyl-2-(benzylcarbamoyl)hydrazinyl)-2-methylpropanoate (Compound V-1) (958.2 mg, 3.0 mmol) in tetrahydrofuran/methanol/water (2:3:1, 15 ml), lithium hydroxide monohydrate (251.8 mg, 6.0 mmol) was added and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with water (25 ml) and washed with ether (25 ml). The aqueous layer was acidified with 10%-citric acid (15 ml) and extracted with chloroform (30 ml). The organic layer was washed with brine (25 ml) and dried over magnesium sulfate and then filtered. The filtrate was concentrated in vacuo to obtain the title compound (724 mg, 83%).

Workup

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

Sources & evidence

ORD record
ord-7e27a40edcc84a1c86b456e01fd1cabd
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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