Sodium Hydroxide → HCID 9951149, compound

HRID 2233356Notes

Reaction equation

HRID 2233356 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13](=[O:25])[NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([O:23]C)=[O:22])=[CH:17][N:16]=3)[CH:10]=[C:9]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:7]=2[CH:8]=1.CO.C1COCC1>O>[CH3:3][C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13](=[O:25])[NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][N:16]=3)[CH:10]=[C:9]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67485648HCID 67485648, compound

Product 1

HCID 9951149HCID 9951149, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide solution (0.94 ml of 1M, 0.94 mM) was added to a solution of 2-methyl-4-isobutoxy-6-[N-(5-methoxycarbonylpyridin-2-yl)carbamoyl]benzofuran (Method 1; 120 mg, 0.314 mM) in a methanol/THF mixture (1 ml+4 ml), and the resulting solution stirred at ambient temperature. After 4 hrs the reaction mixture was diluted with water (5 ml) and concentrated to half volume in vacuo. The resulting mixture was acidified to pH6 with 1M HCl. The resulting solid precipitate was filtered, washed with water, and dried to give a pale cream solid. This was chromatographed (10 g Bondelut), eluting with DCM containing methanol (0-10% gradient) to give the title compound as a colourless solid. NMR: 1.03 (d, 6H), 2.09 (sept, 1H), 2.45 (s, 3H), 3.97 (d, 2H), 6.66 (s, 1H), 7.44 (s, 1H), 7.85 (s, 1H), 8.31 (t, 2H), 8.87 (s, 1H), 11.10 (bs, 1H); m/z 367 (M+H)+.

Workup

  1. concentrationconcentrated to half volume in vacuo
  2. filtrationThe resulting solid precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customto give a pale cream solid
  6. customThis was chromatographed (10 g Bondelut)
  7. washeluting with DCM
  8. additioncontaining methanol (0-10% gradient)

Sources & evidence

ORD record
ord-fa084a2051cf4c4fb2498887d04ea68b
Source dataset
uspto-grants-2010_05
Patent number
US07709505B2

Reaction notes

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