Hydrochloric Acid → HCID 22615054, compound

HRID 843156Notes

Reaction equation

HRID 843156 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH:18]([OH:24])[CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[C:9]=2[C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].Cl>CO>[OH:24][CH:18]([CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[CH2:17][O:16][C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 489104HCID 489104, compound

Product 1

HCID 22615054HCID 22615054, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (100 mg) in methanol (5 ml) was treated with 5 N NaOH solution (1 ml) at room temperature, and the resulting mixture was stirred overnight at the same temperature. The solution was acidified with 1N HCl solution (6 ml) and concentrated in vacuo. The residue was dissolved in H2O and passed through Sep-Pak Cartridge (C18) which was developed with H2O-MeOH. The fractions containing the target compound were collected and concentrated in vacuo to give 4-(2-hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid (79 mg) as a white powder. FAB-MS: m/z 308 (MH+); 1H-NMR (DMSO-d6): δ 1.05 (6H, d, J=6 Hz), 2.65 (3H, s), 2.73 (1H, dd, J1=12 Hz, J2=7 Hz), 2.86 (2H, m), 3.99 (1H, m), 4.16 (2H, d, J=5 Hz), 6.68 (1H, d, J=8 Hz), 7.01 (1H, d, J=8 Hz), 7.17 (1H, t, J=8 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in H2O
  3. additionThe fractions containing the target compound
  4. customwere collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0be45c60cb948dd99426a866fa1e1ce
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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