Potassium Hydroxide → Potassium (4R)-4-(3,3-dimethylbutyl)-4-methyl-2-{7-[(methylsulfonyl)amino]-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl}-3-oxo-3,4-dihydronaphthalen-1-olate

HRID 2224997Notes

Reaction equation

HRID 2224997 reaction equation
[CH3:1][C:2]([CH3:36])([CH3:35])[CH2:3][CH2:4][C@:5]1([CH3:34])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=3[S:18](=[O:32])(=[O:31])[N:17]=2)[C:6]1=[O:33].[OH-].[K+:38]>C(O)C.O>[CH3:1][C:2]([CH3:36])([CH3:35])[CH2:3][CH2:4][C@:5]1([CH3:34])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O-:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=3[S:18](=[O:32])(=[O:31])[N:17]=2)[C:6]1=[O:33].[K+:38]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 135430231Methanesulfonamide, N-(3-((4R)-4-(3,3-dimethylbutyl)-3,4-dihydro-1-hydroxy-4-methyl-3-oxo-2-naphthalenyl)-1,1-dioxido-2H-1,2,4-benzothiadiazin-7-yl)-

Product 1

HCID 86598023Potassium (4R)-4-(3,3-dimethylbutyl)-4-methyl-2-{7-[(methylsulfonyl)amino]-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl}-3-oxo-3,4-dihydronaphthalen-1-olate

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
55 °C

Procedure

Placed 245.12 mg of the product of Example 49-7 into a 10 mL receiver flask. Added 6 mL of 50/50 ethanol/water. Warmed to in an oil bath on a hot-plate set to 90° C. and added 29.02 mg of potassium hydroxide. Solution clarified. Cooled in 10° C. increments to 55° C. Solid precipitated. Cooled to 40° C. and held for ˜1 hour. Cooled to ambient temperature and stirred overnight. Collected solid via vacuum filtration the next morning and dried the solid at 50° C./vacuum for 3 days.

Workup

  1. temperatureWarmed to in an oil bath on
  2. customa hot-plate set to 90° C.
  3. customSolid precipitated
  4. temperatureCooled to 40° C.
  5. temperatureCooled to ambient temperature
  6. customCollected solid
  7. filtrationvia vacuum filtration the next morning
  8. customdried the solid at 50° C./vacuum for 3 days

Sources & evidence

ORD record
ord-f5c0d4a40ddf40acbe648b3c0f4258fe
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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