Hydrochloric Acid → HCID 59556627, compound

HRID 1172982Notes

Reaction equation

HRID 1172982 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]\[C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].Cl>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]\[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59556579HCID 59556579, compound

Product 1

HCID 59556627HCID 59556627, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (Z)-methyl 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)acrylate (30 mg, 0.075 mmol) in EtOH (2 mL) was added 2N aqueous NaOH (2 mL). The reaction was stirred at room temperature, under nitrogen, for 2 hours. Reaction was acidified via addition of 1N HCl, until a precipitate formed. Solid was collected by filtration, washed with 0.2N HCl, and dried in a vac oven to give (Z)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)acrylic acid (8.2 mg, 28.3%). LCMS (Table 1, Method c) Rt=2.64 min, m/z 385.12 (M+H)+. 1H NMR (400 MHz, DMSO) δ ppm 13.11-12.20 (m, 1H), 8.15 (d, 2H), 8.04 (d, 1H), 7.99 (dd, 1H), 7.78 (d, 2H), 7.37 (d, 1H), 7.03 (d, 1H), 6.12 (d, 1H), 4.81 (sept., 1H), 1.33 (d, 6H)

Workup

  1. customReaction
  2. customformed
  3. filtrationSolid was collected by filtration
  4. washwashed with 0.2N HCl
  5. customdried in a vac oven

Sources & evidence

ORD record
ord-b75548cfbc7048a5947f9ba3a6adcb30
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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