Lithium Hydroxide → HCID 59483830, compound

HRID 1808351Notes

Reaction equation

HRID 1808351 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][N:16]3[CH:19]=[N:20][C:21]([C:22]([O:24]C)=[O:23])=[C:15]3[CH2:14]2)(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1.[Li+].[OH-]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:26])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][N:16]3[CH:19]=[N:20][C:21]([C:22]([OH:24])=[O:23])=[C:15]3[CH2:14]2)(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68509742HCID 68509742, compound

Product 1

HCID 59483830HCID 59483830, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 7-(4-methoxy-2,6-dimethylphenylsulfonyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate (0.13 mmol, 1 equiv.), MeOH/H2O (1:1, 4 ml), and LiOH (0.551 mmol, 6 equiv.) was stirred for 16 h at 25° C. The organic solvent was removed in vacuo, and the resulting suspension was diluted with water (5 ml) and adjusted to an acidic pH value with 1N HCl at 0° C. Extraction with ethyl acetate (2×15 ml) was then carried out, and the combined organic phases were washed with sat. NaCl solution. The organic phase was dried over Na2SO4 and concentrated in vacuo to yield the product in the form of a light-yellow solid. This was used in the following stage without further purification. Yield: 63%

Workup

  1. customThe organic solvent was removed in vacuo
  2. additionthe resulting suspension was diluted with water (5 ml)
  3. customadjusted to an acidic pH value with 1N HCl at 0° C
  4. extractionExtraction with ethyl acetate (2×15 ml)
  5. washthe combined organic phases were washed with sat. NaCl solution
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto yield the product in the form of a light-yellow solid
  9. customThis was used in the following stage without further purification

Sources & evidence

ORD record
ord-2b2b7f52c487406a8d3acac9ee78ba82
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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