Hydrochloric Acid → HCID 178527343, compound

HRID 2215108Notes

Reaction equation

HRID 2215108 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[S:11]([N:14]([CH2:27][C:28]1[N:32](CCC#N)[N:31]=[N:30][N:29]=1)[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[CH2:23][CH2:22][CH2:21]2)(=[O:13])=[O:12].Cl>O1CCCC1>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[S:11]([N:14]([CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[CH2:23][CH2:22][CH2:21]2)[CH2:27][C:28]1[NH:32][N:31]=[N:30][N:29]=1)(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68570377HCID 68570377, compound

Product 1

HCID 178527343HCID 178527343, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 M NaOH solution (0.63 mmol, 1.0 eq) is added to a stirred solution of 2,4-dichloro-N-[1-(2-cyano-ethyl)-1H-tetrazol-5-ylmethyl]-N-[2-(indan-5-yloxy)-ethyl]benzene sulfonamide (0.325 g, 1 eq.) in tetrahydrofuran (3 ml) at room temperature and the reaction mixture stirred overnight. The reaction mixture is acidified with 1 M HCl solution to pH 3, and then extracted with EtOAc (20 ml). The organic extract is washed with 1 M HCl solution (2×5 ml), and then with brine (1×10 ml), dried over MgSO4, and concentrated to give a crude solid (0.211 g), which is triturated with Et2O, filtered, washed with Et2O and dried under suction. The solid is purified by preparative HPLC to give pure 2,4-dichloro-N-[2-(indan-5-yloxy)-ethyl]-N-(1H-tetrazol-5-ylmethyl)benzene-sulfonamide.

Workup

  1. extractionextracted with EtOAc (20 ml)
  2. extractionThe organic extract
  3. washis washed with 1 M HCl solution (2×5 ml)
  4. dry with materialwith brine (1×10 ml), dried over MgSO4
  5. concentrationconcentrated
  6. customto give a crude solid (0.211 g), which
  7. customis triturated with Et2O
  8. filtrationfiltered
  9. washwashed with Et2O
  10. customdried under suction
  11. customThe solid is purified by preparative HPLC

Sources & evidence

ORD record
ord-4175f4f35a6140d1a2e366a75327e879
Source dataset
uspto-grants-2006_09
Patent number
US07109203B2

Reaction notes

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