Sodium Hydroxide → 5-(3-((3-(3-Chloro-phenyl)-propyl)-(Pyridine-3-sulfonyl)-amino)-propyl)-thiophene-2-carboxylic acid

HRID 2117470Notes

Reaction equation

HRID 2117470 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][N:13]([CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)[S:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])=[CH:8][CH:9]=1)=[O:4].[OH-].[Na+]>CCO>[Cl:32][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][CH2:23][N:13]([S:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:12][CH2:11][CH2:10][C:7]2[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=2)[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 536947585-(3-((3-(3-Chloro-phenyl)-propyl)-(Pyridine-3-sulfonyl)-amino)-propyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 183760725-(3-((3-(3-Chloro-phenyl)-propyl)-(Pyridine-3-sulfonyl)-amino)-propyl)-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(3-((3-(3-chloro-phenyl)-propyl)-(pyridine-3-sulfonyl)-amino)-propyl)-thiophene-2-carboxylic acid methyl ester prepared of Example 4, Step B (0.119 g, 0.241 mmol), in 5 mL EtOH and 0.72 mL 1N NaOH was stirred at room temperature overnight. The reaction mixture was adjusted to pH 6.2 and the layers were separated. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound (16 mg). 1H NMR (400 MHz, CDCl3) δ 8.00 (d, 1H, J=8), 7.70 (d, 1H, J=4), 7.30-7.60 (m, 6H), 6.75 (d, 1, J=4), 3.20 (m, 4H), 2.95 (t, 2H, J=7), 2.60 (t, 2H, J=7), 1.70-2.00 (m, 4H); MS 478 (M+1), 476 (M−1).

Workup

  1. customthe layers were separated
  2. washThe organic solution was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5ba019d84af421a995cbf47d2880229
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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