Hydrogen Peroxide → HCID 70064879, compound

HRID 1654744Notes

Reaction equation

HRID 1654744 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]([CH2:22][CH2:23][S:24][CH3:25])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1.[OH2:26].[OH:27]O>C(O)(=O)C>[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]([CH2:22][CH2:23][S:24]([CH3:25])(=[O:27])=[O:26])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 70062372HCID 70062372, compound

Product 1

HCID 70064879HCID 70064879, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(±)-3-[[5-[4-(Aminoiminomethyl)phenyl]-1oxopentyl]amino]-5-(methylthio)pentanoic acid (2.5 g) was added to water (15 ml) and acetic acid (5 ml) and 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) δ1.51 (m, 4H), 1.56 (m, 2H), 2.0 (m, 2H), 2.10 (s, 3H), 2.90 (m, 4H), 2.71 (m, 2H), 4.10 (m, 1H), 7.35 (m, 9H), 7.7 (bd, 1H, J=7.9 Hz), 9.10 (bs, 2H), 9.25 (bs, 2H); MS (FAB) m/e 398.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-7167e5e45f4a46259d899624dc82fcc0
Source dataset
uspto-grants-1995_04
Patent number
US05409939

Reaction notes

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