Lithium Hydroxide → HCID 19978636, compound

HRID 2403994Notes

Reaction equation

HRID 2403994 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[N:10]([CH2:20][CH3:21])[CH2:11][CH2:12][NH:13]C(=O)C(F)(F)F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>CO.O>[CH2:1]([O:8][C:9](=[O:22])[N:10]([CH2:11][CH2:12][NH2:13])[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58480331HCID 58480331, compound

Product 1

HCID 19978636HCID 19978636, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound N (24.9 g, 78.2 mmol) in MeOH (300 ml) was added a solution of LiOH (3.8 g, 156 mmol) in water (30 ml). The reaction mixture was stirred at room temperature for 5 h. Next the solvents were evaporated to ¾ of initial volume followed by the dilution with water (200 ml). The solution was extracted with EtOAc (200 ml×2) and the organic layer was washed with brine (100 ml), dried over MgSO4 and evaporated in vacuo. Residue was dissolved in ether (200 ml) and treated with 2 N HCl/ether (200 ml). The formed precipitate was filtered, washed with ether and dried in vacuum to provide hydrochloride salt of compound O (12.1 g, 46.7 mmol) as white solid. LC-MS [M+H] 222.9 (C12H18N2O2+H, calc: 223.2).

Workup

  1. customNext the solvents were evaporated
  2. extractionThe solution was extracted with EtOAc (200 ml×2)
  3. washthe organic layer was washed with brine (100 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. dissolutionResidue was dissolved in ether (200 ml)
  7. additiontreated with 2 N HCl/ether (200 ml)
  8. filtrationThe formed precipitate was filtered
  9. washwashed with ether
  10. customdried in vacuum

Sources & evidence

ORD record
ord-c576a3379ee440d2981a1fa0707578cf
Source dataset
uspto-grants-2014_08
Patent number
US08802681B2

Reaction notes

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