Hydrogen Peroxide → HCID 46181891, compound

HRID 709183Notes

Reaction equation

HRID 709183 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-e690b3552f1a46d8ae36220fd9344743
Source dataset
uspto-grants-2015_11
Patent number
US09180119B2

Reaction notes

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