Sodium Hydroxide → (3-(((2-(3-Chloro-phenoxy)-ethyl)-(pyridine-3-sulfonyl)-amino)-methyl)-phenyl)-acetic acid

HRID 2300418Notes

Reaction equation

HRID 2300418 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][N:12]([CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[S:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH:6]=1.[OH-].[Na+]>CO>[Cl:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[O:24][CH2:23][CH2:22][N:12]([CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[CH:10]=[CH:9][CH:8]=1)[S:13]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53728724(3-(((2-(3-Chloro-phenoxy)-ethyl)-(Pyridine-3-sulfonyl)-amino)-methyl)-phenyl)-acetic acid methyl ester

Product 1

HCID 18376084(3-(((2-(3-Chloro-phenoxy)-ethyl)-(pyridine-3-sulfonyl)-amino)-methyl)-phenyl)-acetic acidYield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the compound of Example 2, Step A (0.025 g, 0.053 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 (20 mg). 1H NMR (400 MHz, CDCl3) δ 9.05 (s, 1H), 8.77 (d, 1H), 8.11 (d, 1H), 7.43 (m, 1H), 7.08-7.27 (m, 5H), 6.89 (d, 1H), 6.62 (s, 1H), 6.55 (d, 1H), 4.51 (s, 2H), 3.95 (t, 2H), 3.59 (s, 4H); MS 495 (M−2).

Workup

  1. customThe mixture was quenched with 2N HCl
  2. additionwas diluted with CH2Cl2
  3. washThe organic layer was 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-84bc1e3f8e1941e3a507eff2ef0f483a
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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