Lithium hydroxide, monohydrate → HCID 53397486, compound

HRID 2361945Notes

Reaction equation

HRID 2361945 reaction equation
[CH2:1]([NH:8][C:9](=[O:20])[NH:10][CH2:11][C:12]1([C:15]([O:17]CC)=[O:16])[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.CO.O.O>[CH2:1]([NH:8][C:9](=[O:20])[NH:10][CH2:11][C:12]1([C:15]([OH:17])=[O:16])[CH2:14][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67448806HCID 67448806, compound

Product 1

HCID 53397486HCID 53397486, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To the solution of ethyl 1-((3-benzylureido)methyl)cyclopropanecarboxylate (Compound V-3) (1.6 g, 5.8 mmol) in tetrahydrofuran/methanol/water (2:3:1, 20 ml), lithium hydroxide monohydrate (487 mg, 11.6 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 (1.08 g, 77%).

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-b885e61356d94f08b702b335f00b0675
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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