Hydrochloric Acid → HCID 44547912, compound

HRID 1512888Notes

Reaction equation

HRID 1512888 reaction equation
[OH-].[Na+].[CH2:3]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]([CH3:30])[CH3:29])=[C:23]([Cl:31])[CH:22]=3)[O:18][N:17]=2)[C:9]([CH2:32][CH2:33][C:34]([O:36]CCC)=[O:35])=[CH:8]1)[CH2:4][CH2:5][CH3:6].Cl>O1CCCC1.C(O)(C)C.O>[CH2:3]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]([CH3:30])[CH3:29])=[C:23]([Cl:31])[CH:22]=3)[O:18][N:17]=2)[C:9]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[CH:8]1)[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67025237HCID 67025237, compound

Product 1

HCID 44547912HCID 44547912, compoundYield 53.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (94 mg) was added to a solution of propyl 3-[1-butyl-7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D123) (61 mg) in tetrahydrofuran (5 mL), isopropanol (4 mL) and water (2 mL). The reaction mixture was stirred at room temperature overnight. The mixture was neutralized with 2 M HCl till pH ˜6.0. The solvent was concentrated, and the residue was dissolved in water. The precipitated solid was purified by Mass Directed Auto Prep to afford 3-[1-butyl-7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid (E29) (30 mg). δH (DMSO-d6, 400 MHz): 0.65 (3H, t), 0.96 (2H, m), 1.37 (8H, m), 2.62 (2H, t), 2.98 (2H, t), 4.10 (2H, t), 4.88 (1H, m), 7.17 (1H, t), 7.25 (1H, s), 7.44 (2H, m), 7.81 (1H, dd), 8.13 (1H, dd), 8.19 (1H, d), 12.05 (1H, br s); MS (ES): C26H28ClN3O4 requires 481; found 482.2 (M+H+).

Workup

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in water
  3. customThe precipitated solid was purified by Mass Directed Auto Prep

Sources & evidence

ORD record
ord-d00b689b9cd94b3b9892fe01b884f197
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

Loading…