Hydrogen Peroxide → HCID 72194746, compound

HRID 1477240Notes

Reaction equation

HRID 1477240 reaction equation
[OH:1][NH:2][C:3](=[O:28])[C@@H:4]([NH:10][C:11](=[O:27])[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]#[C:21][C@@H:22]2[CH2:24][C@H:23]2[CH2:25][OH:26])=[CH:14][CH:13]=1)[C:5]([CH3:9])([S:7][CH3:8])[CH3:6].[OH:29]O>C(#N)C.O>[OH:1][NH:2][C:3](=[O:28])[C@@H:4]([NH:10][C:11](=[O:27])[C:12]1[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]#[C:21][C@@H:22]2[CH2:24][C@H:23]2[CH2:25][OH:26])=[CH:16][CH:17]=1)[C:5]([CH3:9])([S:7]([CH3:8])=[O:29])[CH3:6]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 118659441HCID 118659441, compound

Product 1

HCID 72194746HCID 72194746, compoundYield 89,800%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a stirring solution of N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)benzamide (3, 0.2 g, 0.50 mmol) in acetonitrile/water (20 mL) was added 30% aqueous hydrogen peroxide (0.015 mL, 0.50 mmol) and the reaction mixture was stirred at room temperature for 18 hr. The reaction mixture was lyophylized to afford N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)benzamide (4, 200 mg, 449 mmol, 90%). MS: m/z calcd for C21H24N2O5S 416.14. found [M+H]+ 417.

Sources & evidence

ORD record
ord-e251b64634a145bd8ef378829316d6d2
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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