Lithium Hydroxide → HCID 71282048, compound

HRID 1481766Notes

Reaction equation

HRID 1481766 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([C:18]2[NH:23][C:22](=[O:24])[C:21]([C:25]([O:27]C)=[O:26])=[CH:20][C:19]=2[CH2:29][CH3:30])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1>[CH2:1]([O:8][C:9]1[C:17]([C:18]2[NH:23][C:22](=[O:24])[C:21]([C:25]([OH:27])=[O:26])=[CH:20][C:19]=2[CH2:29][CH3:30])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71284303HCID 71284303, compound

Product 1

HCID 71282048HCID 71282048, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 6-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (0.0888 g, 0.21 mmol) in THF (1.5 mL) was added a solution of LiOH (1M aqueous saturated, 0.60 ml, 0.60 mmol). The reaction mixture was heated at 50° C. for 1 h until starting material was consumed. The reaction was then cooled to room temperature and acidified with 1M HCl to pH˜2. The product was extracted with DCM (3×10 mL). The combined organic phases were washed with brine and dried over Na2SO4. Upon removal of the solvent product (0.0757 g, 88%) was obtained as yellow solid.

Workup

  1. customwas consumed
  2. temperatureThe reaction was then cooled to room temperature
  3. extractionThe product was extracted with DCM (3×10 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. customUpon removal of the solvent product (0.0757 g, 88%)
  7. customwas obtained as yellow solid

Sources & evidence

ORD record
ord-bed9c3e3c5c24efcb0f0ef13122f018d
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

Loading…