Hydrogen Peroxide → HCID 70065773, compound

HRID 1654745Notes

Reaction equation

HRID 1654745 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([CH3:30])=[O:29])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1.[OH2:31].OO>C(O)(=O)C>[NH2:1][N:2]=[CH:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([CH3:30])(=[O:31])=[O:29])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 70063931HCID 70063931, compound

Product 1

HCID 70065773HCID 70065773, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(±)-β-[[5-[4-(Aminoiminomethyl)phenyl]-1-oxopentyl]amino]-2-(methylsulfinyl)benzenepropanoic acid (2.5 g) was added to water (15 ml), acetic acid (5 ml) and followed by the addition of 30% H2O2 (10 mL). The oxidation was allowed to proceed for 48 hours after which the reaction mixture was purified by reverse phase chromatography (water/acetonitrile) and lyophilized to give 1.6 g of the title compound as a white solid: 1H NMR (d6 -DMSO) δ1.52 (m, 4H), 2.01 (m, 2H), 2.63 (m, 4H), 3.50 (s, 3H), 5.82 (m, 1H), 7.35 (m, 9H), 7.7 (m, 1H), 9.10 (bs, 2H), 9.20 (bs, 2H); MS (FAB) m/e 446.2 (M+H+).

Workup

  1. customafter which the reaction mixture was purified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record
ord-5cd8a1f41f974f48bc5d8dd635f1246b
Source dataset
uspto-grants-1995_04
Patent number
US05409939

Reaction notes

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