Sodium Hydroxide → HCID 178441775, compound

HRID 1742407Notes

Reaction equation

HRID 1742407 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:32][CH2:33][CH2:34][CH3:35])[N:9]([CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[C:10]=1[Cl:11])=[O:5])C.[OH-].[Na+]>C(O)C>[CH2:32]([C:8]1[N:9]([CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[C:10]([Cl:11])=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1)[CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178441773HCID 178441773, compound

Product 1

HCID 178441775HCID 178441775, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-butyl-5-chloro-1-{5-[2-(1H-tetrazol-5-yl)-phenyl]-indan -1-yl}-1H-imidazole-4-carboxylic acid ethyl ester (50 mg, 0.1 mmol)in ethanol (2 mL) was added 2N sodium hydroxide (NaOH) (0.5 mL). The reaction mixture was stirred for 20 hours, and then concentrated in vacuo. The residue was diluted with saturated aqueous NaCl (10 mL) and neutralized with concentrated acetic acid (HOAc). The aqueous solution was extracted with chloroform (CHCl3) (3×10 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was dissolved in EtOAc (0.5 mL) and hexanes were added to precipitate the product. The solid was filtered and dried in vacuo. 1H NMR (250 MHz, d6 -DMSO): d 7.62 (m, 5 H), 7.08 (s, t), 6.85 (m, 2 H), 6.15 (m, 1 H), 3.1-2.0 (m), 165 (m, 2 H), 140 (m, 2 H), 0.95 (t, 3 H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with saturated aqueous NaCl (10 mL) and neutralized with concentrated acetic acid (HOAc)
  3. extractionThe aqueous solution was extracted with chloroform (CHCl3) (3×10 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in EtOAc (0.5 mL)
  7. additionhexanes were added
  8. customto precipitate the product
  9. filtrationThe solid was filtered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-31775fef2aa249049556ad04d61d1411
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

Loading…