Potassium Hydroxide → HCID 87955284, compound

HRID 1815490Notes

Reaction equation

HRID 1815490 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([O:29]CC)=[O:28])[CH2:22]2)=[O:20])=[CH:13][C:12]=1[Cl:32])[CH3:2].[OH-].[Na+].[OH-].[K+]>CO>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([OH:29])=[O:28])[CH2:22]2)=[O:20])=[CH:13][C:12]=1[Cl:32])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 11547392HCID 11547392, compound

Product 1

HCID 87955284HCID 87955284, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

The compound of Example 137 was hydrolyzed using an excess of aqueous 10% NaOH in methanol, stirring overnight. The reaction mixture was concentrated in vacuo, water was added, and the solution was extracted with ether. The mixture was acidified; the resultant solid was collected by filtration and dried overnight in a vacuum oven, giving a white solid, m.p. 166-171C. 1H-NMR (DMSO 300 MHz) δ 1.17 (t, J=7 Hz, 3H), broad peaks totaling 9 protons at 1.32-1.48, 1.51-1.78, 1.90-2.04, 2.25-2.50, 2.80-2.90, 2.95-3.17, 3.45-3.51, 3.95-4.19, 4.41-4.51, 4.06 (q, J=7 Hz, 1H), 6.80 (d, J=9 Hz, 1H), 7.01 (t, J=7 Hz, 1H), 7.15 (d, J=8 Hz, 1H), 7.26-7.40 (m, 2H), 7.40-7.48 (m, 1H), 7.51 (dd, J=9 Hz, 2 Hz, 1H), 7.99 (d, J=9 Hz, 1H). Anal. Calcd. for C23H24ClNO4S: C, 61.94; H, 5.42; N, 3.14. Found: C, 61.75; H, 5.65; N, 3.15. The resultant acid (303 mg, 0.631 mmol) was dissolved in 3 mL MeOH. A KOH solution (38 mg, 0.595 mmol, of 87.6% KOH) in 1 ml MeOH was added. The resulting solution was concentrated in vacuo, and 5 mL ether was added. The mixture was stirred for one hour to form a powder, which was filtered and dried in the vacuum oven at 60C to yield 307 mg of a solid, water soluble product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, water
  2. additionwas added
  3. extractionthe solution was extracted with ether
  4. filtrationthe resultant solid was collected by filtration
  5. customdried overnight in a vacuum oven
  6. customgiving a white solid, m.p. 166-171C
  7. concentrationThe resulting solution was concentrated in vacuo, and 5 mL ether
  8. additionwas added
  9. stirringThe mixture was stirred for one hour
  10. customto form a powder, which
  11. filtrationwas filtered
  12. dry with materialdried in the vacuum oven at 60C

Sources & evidence

ORD record
ord-6379ef20e2d041c4aa23e8d8092cf524
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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