Sodium Methoxide → HCID 9933752, compound

HRID 361466Notes

Reaction equation

HRID 361466 reaction equation
[C:1]([C:4]([CH3:39])([CH3:38])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([S:18]([N:21](C(OCC(C)C)=O)[C:22]3[C:27]([O:28][CH3:29])=[N:26][C:25]([CH3:30])=[CH:24][N:23]=3)(=[O:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)([OH:3])=[O:2].C[O-].[Na+]>CO>[C:1]([C:4]([CH3:39])([CH3:38])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([S:18]([NH:21][C:22]3[C:27]([O:28][CH3:29])=[N:26][C:25]([CH3:30])=[CH:24][N:23]=3)(=[O:19])=[O:20])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21186306HCID 21186306, compound

Product 1

HCID 9933752HCID 9933752, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[4-(2-carboxy-2-methylpropyl)phenyl]-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (334 mg) was dissolved in methanol (10 ml) and sodium methoxide (324 mg) was added. The solution was heated to reflux for 4 hours, cooled and evaporated to dryness. The residue was partitioned between water (20 ml) and ethyl acetate (15 ml) and the organic layer was separated and washed with water (20 ml). The combined aqueous phases were acidified with 2M hydrochloric acid and extracted with ethyl acetate (3×25 ml). The combined organic extracts were dried (MgSO4) and evaporated. The residue was triturated with isohexane to give 2-[4-(2-carboxy-2-methylpropyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (117 mg); 1H NMR (d6 -DMSO): 1.1 (s, 6 H), 2.24 (s, 3 H), 2.85 (br, 2 H), 3.80 (s, 3 H); 7.13 (br, 2 H), 7.35 (br d, 2 H), 7.50 (br s, 1 H), 7.57 (q, 1 H), 8.78 (dd, 1 H), 10.41 (br s, 1 H); mass spectrum (+ve ESP) 457.2 (M+H)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 4 hours
  3. temperaturecooled
  4. customevaporated to dryness
  5. customThe residue was partitioned between water (20 ml) and ethyl acetate (15 ml)
  6. customthe organic layer was separated
  7. washwashed with water (20 ml)
  8. extractionextracted with ethyl acetate (3×25 ml)
  9. dry with materialThe combined organic extracts were dried (MgSO4)
  10. customevaporated
  11. customThe residue was triturated with isohexane

Sources & evidence

ORD record
ord-ef976740ec154c9e89aea52748379df6
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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