Lithium Hydroxide → HCID 69652404, compound

HRID 2212207Notes

Reaction equation

HRID 2212207 reaction equation
[Li+].[OH-].C([O:5][C:6]([CH:8]1[CH2:13][CH:12]([N:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:24])[C:18]=3[C:17]3=[N:25][O:26][C:27]([CH3:28])=[C:16]3[C:15]2=[O:29])[CH2:11][N:10]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:9]1)=[O:7])C>O.O1CCOCC1>[C:33]([O:32][C:30]([N:10]1[CH2:11][CH:12]([N:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:24])[C:18]=3[C:17]3=[N:25][O:26][C:27]([CH3:28])=[C:16]3[C:15]2=[O:29])[CH2:13][CH:8]([C:6]([OH:7])=[O:5])[CH2:9]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69652406HCID 69652406, compound

Product 1

HCID 69652404HCID 69652404, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Add a solution of LiOH (370 mg, 15.5 mmol) in water (50 mL) to a solution of 5-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolinyl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.5 g, 3.1 mmol) in dioxane (50 mL). Stir 4 H at room temperature and concentrate to dryness. Partition between 20% iPrOH/CHCl3 and water. Acidify to pH 1 with 5N HCl. Extract 2× with 20% iPrO/CHCl3. Wash combined organics with brine, dry over Na2SO4, filter, and concentrate to dryness to afford the title compound (1.43 g, 100%) as a yellow foam as a mixture of cis isomers. MS(IS) 460.4 (M−1); TLC (10% MeOH/CHCl3) Rf=0.31.

Workup

  1. concentrationconcentrate to dryness
  2. customPartition between 20% iPrOH/CHCl3 and water
  3. extractionExtract 2× with 20% iPrO/CHCl3
  4. washWash
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-858145c44c244f11a51e28f6b75e2606
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

Loading…