Hydrogen Peroxide → HCID 46181891, compound

HRID 2280283Notes

Reaction equation

HRID 2280283 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=4[CH3:23])[C:13]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[CH:12][CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-:32].[K+].[K+].OO.O>CS(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21](=[O:32])[NH2:22])=[CH:17][C:16]=4[CH3:23])[C:13]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:12][CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 67175633HCID 67175633, compound

Product 1

HCID 46181891HCID 46181891, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of ethyl 3-(5-(benzo[d][1,3]dioxol-5-yl)-1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (100 mg, 0.249 mmol) and potassium carbonate (52 mg, 0.373 mmol) in DMSO (1 mL) was added 30% aqueous H2O2 (28.2 mg, 0.249 mmol). The resultant mixture was stirred at room temperature for 2 h. TLC showed the reaction was completed. Water (7 mL) was added and white solid precipitated. The suspension was centrifuged and the aqueous phase was discarded. The resultant solid was dried in vacuum to afford the amide intermediate as a white solid (85 mg, yield 81%). To the mixture of this intermediate in H2O (0.6 mL) and THF (0.6 mL) was added LiOH.H2O (10 mg, 0.238 mmol). The reaction mixture was stirred at room temperature overnight. THF was evaporated in vacuum. The residue was acidified to pH=4 with 5% hydrochloric acid, centrifuged and dried to afford 3-(5-(benzo[d][1,3]dioxol-5-yl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoic acid as a white solid (46 mg, overall yield 47%).

Workup

  1. customwhite solid precipitated
  2. customThe resultant solid was dried in vacuum

Sources & evidence

ORD record
ord-1aa840600a2e49b59e6a6d3b0eaa6b77
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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