Sodium Hydroxide → 7-((4-Butyl-benzyl)-(pyridine-3-sulfonyl)-amino)-heptanoic acid

HRID 2117465Notes

Reaction equation

HRID 2117465 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=1)[S:11]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12].[OH-].[Na+]>CO>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:10]([S:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:31])=[O:2])=[CH:26][CH:25]=1)[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 538614617-((4-Butyl-benzyl)-(Pyridine-3-sulfonyl)-amino)-heptanoic acid methyl ester

Product 1

HCID 183762267-((4-Butyl-benzyl)-(pyridine-3-sulfonyl)-amino)-heptanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-((4-butyl-benzyl)-(pyridine-3-sulfonyl)-amino)-heptanoic acid methyl ester prepared of Example 1, Step B (0.040 g, 0.158 mmol), in 2 mL MeOH and 0.5 mL 2N NaOH was stirred at room temperature overnight. The mixture was quenched with 2N HCl and was diluted with CH2Cl2 The organic layer was washed with 1N HCl and water, dried over MgSO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica gel (2% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2) to afford the title compound (42 mg). 1H NMR (400 MHz, CDCl3) δ 9.09 (s, 1H), 8.77 (d, 1H), 8.08 (d, 1H), 7.48 (dd, 1H), 7.09 (m, 4H), 4.32 (s, 2H), 3.12 (s, 2H), 2.55 (t, 2H), 2.25 (t, 2H), 1.12-1.58 (m, 12H), 0.88 (t, 3H); MS 431 (M−1).

Workup

  1. customThe mixture was quenched with 2N HCl
  2. additionwas diluted with CH2Cl2 The organic layer
  3. washwas washed with 1N HCl and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography on silica gel (2% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6f87c96c64404aa0bf59e4e4da2ea038
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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