Sodium Hydroxide → Sodium 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoate

HRID 1512869Notes

Reaction equation

HRID 1512869 reaction equation
[OH-].[Na+:2].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[CH:22]4)[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]>C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH2:28][CH2:29][C:30]([O-:32])=[O:31])=[CH:22]4)[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].[Na+:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59146126ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoate

Product 1

HCID 67094369Sodium 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous NaOH solution (2 N, 2 mL) was added to a solution of ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoate (D33) (90 mg) in ethanol (20 mL) at RT. The resulting solution was stirred for 30 min. Ethanol was evaporated. Saturated aqueous sodium chloride solution (10 mL) was added. The mixture was extracted with EtOAc (2×50 mL). The organic fractions were combined. The combined solution was dried over anhydrous magnesium sulfate. The dried solution was concentrated. The residue was triturated with ether to afford sodium 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoate (E9) (80 mg) as a white solid. δH (CD3OD, 400 MHz): 1.44 (6H, d), 2.62 (2H, t), 3.08 (2H, t), 4.87 (1H, m), 6.33 (1H, d), 7.33 (1H, d), 7.41 (1H, d), 7.80 (1H, dd), 8.14 (1H, dd), 8.24 (2H, dd). MS (ES): C22H19ClN3O4Na requires 447; found 425.9 (M—Na++2H+).

Workup

  1. customEthanol was evaporated
  2. additionSaturated aqueous sodium chloride solution (10 mL) was added
  3. extractionThe mixture was extracted with EtOAc (2×50 mL)
  4. dry with materialThe combined solution was dried over anhydrous magnesium sulfate
  5. concentrationThe dried solution was concentrated
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-a2c0546cc02144918a5832f540c9bc22
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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