Hydrochloric Acid → HCID 44548060, compound

HRID 1512892Notes

Reaction equation

HRID 1512892 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[C:26](=[O:34])[CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[C:26](=[O:34])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146159ethyl 4-{7-[5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-3-yl}-4-oxobutanoate

Product 1

HCID 44548060HCID 44548060, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]-4-oxobutanoate (D52) (20 mg) in THF (2 mL) was added aqueous NaOH (2 M, 1 mL), the reaction was stirred at room temperature overnight. The mixture was acidified with aqueous HCl (2M) to pH 4-5, and then partitioned with ethyl acetate (10 mL) and water (10 mL). The organic phase was washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulphate and evaporated to give the crude product, which was purified by Mass Directed Auto Prep to afford 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]-4-oxobutanoic acid (E33) (12 mg). δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 2.59 (2H, t), 3.20 (2H, t), 4.91 (1H, m), 7.41 (1H, t), 7.47 (1H, d), 8.04 (1H, dd), 8.22 (1H, dd), 8.36 (1H, d), 8.41 (1H, d), 8.44 (1H, dd), 11.81 (1H, br s). MS (ES): C23H20ClN3O5 requires 453; found 454.2 (M+H+).

Workup

  1. custompartitioned with ethyl acetate (10 mL) and water (10 mL)
  2. washThe organic phase was washed with water (10 mL) and brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated
  5. customto give the crude product, which
  6. customwas purified by Mass Directed Auto Prep

Sources & evidence

ORD record
ord-b0559812dcae4a57817138831c4dbd90
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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