Hydrogen Peroxide → HCID 53235505, compound

HRID 536621Notes

Reaction equation

HRID 536621 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:11][S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:5]([CH3:27])[CH:4]=1)#[N:2].[OH-:28].[Na+].OO>CS(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:11][S:12][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[C:5]([CH3:27])[CH:4]=1)(=[O:28])[NH2:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67254651HCID 67254651, compound

Product 1

HCID 53235505HCID 53235505, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-(4-(4-cyano-2-methylphenyl)-5-(4-methoxyphenyl)thiophen-3-yl)propanoic acid (30 mg, 0.08 mmol) in DMSO (5 mL) was added NaOH (6 mg, 0.16 mmol), and 30% H2O2 (9 mg, 0.08 mmol). The mixture was stirred at room temperature for 2 h, and purified by preparative HPLC to give 16 mg of the title compound, Example 14 (Scheme III, 17, X1=4-carbamoyl-2-methylphenyl, X2=4-methoxyphenyl) (yield 52%) as a white solid. 1H NMR (CD3OD 400 MHz TMS): δ7.72 (s, 2H), 7.26 (d, J=8.4 Hz, 1H), 7.14 (s, 1H), 7.04 (d, J=8.8 Hz, 2H), 6.70 (d, J=8.4 Hz, 2H), 3.70 (s, 3H), 2.57 (t, J=7.2 Hz, 2H), 2.38 (t, J=8.0 Hz, 2H), 1.96 (s, 3H); MS (ESI): m/z 317.9 [M+23]+.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-2ec2926c617c4cd28f452101fce77480
Source dataset
uspto-grants-2014_10
Patent number
US08859611B2

Reaction notes

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