Lithium hydroxide, monohydrate → HCID 54712199, compound

HRID 908572Notes

Reaction equation

HRID 908572 reaction equation
C([O:8][C:9](=[O:31])[CH2:10][NH:11][C:12]([C:14]1[C:15](=[O:30])[N:16]([CH3:29])[C:17]2[C:22]([C:23]=1[OH:24])=[CH:21][CH:20]=[C:19]([C:25]([O:27]C)=[O:26])[CH:18]=2)=[O:13])C1C=CC=CC=1.O.[OH-].[Li+]>O1CCOCC1.O>[C:9]([CH2:10][NH:11][C:12]([C:14]1[C:15](=[O:30])[N:16]([CH3:29])[C:17]2[C:22]([C:23]=1[OH:24])=[CH:21][CH:20]=[C:19]([C:25]([OH:27])=[O:26])[CH:18]=2)=[O:13])([OH:31])=[O:8]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54712198HCID 54712198, compound

Product 1

HCID 54712199HCID 54712199, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Methyl 3-((2-(benzyloxy)-2-oxoethyl)carbamoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-7-carboxylate (26 mg, 61 μmol) (65689-17-3) was dissolved in 12 ml dioxane/H2O (5:1) and to this was added lithium hydroxide monohydrate (613 μl, 613 μmol) as a 1M aqueous solution. The resultant mixture was heated to 60 C for 4 hrs. The solvent was removed in vacuo and the aqueous layer was acidified with 2N HCl to pH2. Following dilution with EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc (3×). The organic layer was washed with H2O and brine, then dried over Na2SO4. The solvent was removed by rotovap, azeotroping with benzene (3×) to give a light yellow solid which was rinsed with DCM followed by MeOH.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (3×)
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed by rotovap
  7. customazeotroping with benzene (3×)
  8. customto give a light yellow solid which
  9. washwas rinsed with DCM

Sources & evidence

ORD record
ord-d64b41febf5a4658b9ad6a5a512922b2
Source dataset
uspto-grants-2011_09
Patent number
US08017626B2

Reaction notes

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