Hydrochloric Acid → HCID 44546701, compound

HRID 1512930Notes

Reaction equation

HRID 1512930 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]([NH:28][CH2:29][C:30]([O-:32])=[O:31])=[O:27])[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]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:27])[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 86637989HCID 86637989, compound

Product 1

HCID 44546701HCID 44546701, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]carbonyl}glycinate (D96) (50 mg) in THF (5 mL) was added aqueous NaOH (2 M, 2 mL). The reaction was stirred at room temperature overnight. The mixture was acidified with aqueous HCl (2 M) to pH 4-5, partitioned between ethyl acetate (25 mL) and water (25 mL). The organic phase was washed with water (25 mL) and brine (25 mL), dried over anhydrous sodium sulphate and evaporated to give the crude product, which was purified by Mass Directed Auto Prep to afford N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]carbonyl}glycine (E72) (28 mg). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 3.93 (2H, d), 4.90 (1H, m), 7.34 (1H, t), 7.47 (1H, d), 8.00 (1H, dd), 8.23 (2H, m), 8.42 (2H, m), 8.54 (1H, t), 11.55 (1H, s), 12.54 (1H, br s). MS (ES): C22H19ClN4O6 requires 454; found 455.2 (M+H+).

Workup

  1. custompartitioned between ethyl acetate (25 mL) and water (25 mL)
  2. washThe organic phase was washed with water (25 mL) and brine (25 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-f5183210994d486eac3f0c138b70c1b1
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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