Hydrogen Peroxide → HCID 70061944, compound

HRID 1654740Notes

Reaction equation

HRID 1654740 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]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1.[OH2:33].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]([CH2:22][CH2:23][S:24]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)(=[O:33])=[O:25])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 70062192HCID 70062192, compound

Product 1

HCID 70061944HCID 70061944, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(±)-3-[[5-[4-(Aminoiminomethyl)phenyl]-1oxopentyl]amino]-5-[(phenylmethyl)sulfinyl]pentanoic acid (2.5 g) was added to water (15 ml), acetic acid (5 ml) and 30% H2O2 (10 ml). The oxidation was allowed to proceed for 24 h. after which the reaction mixture was worked up. The product 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) δ1.48 (m, 2H), 1.56 (m, 2H), 1.75 (m, 2H), 2.10 (m, 2H), 2.41 (m, 2H), 2.68 (m, 2H), 4.05 (m, 1H), 4.22 (s, 2H), 7.35 (m, 9H), 7.7 (bd, 1H, J=7.9 Hz), 9.10 (bs, 2H), 9.8 (bs, 2H); MS (FAB) m/e 474.2 (M+H+).

Workup

  1. customThe product was purified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record
ord-7d7d6662e80347e3a7e0b9b7c198a0ac
Source dataset
uspto-grants-1995_04
Patent number
US05409939

Reaction notes

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