Acetic Acid → HCID 70062045, compound

HRID 1654741Notes

Reaction equation

HRID 1654741 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][S:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1.C(O)(=[O:33])C.OO>O>[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][S:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)(=[O:33])=[O:24])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 70062232HCID 70062232, compound

Product 1

HCID 70062045HCID 70062045, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(±)-3-[[5-[4-(Aminoiminomethyl)phenyl]-1-oxopentyl]amino]-4-[(phenylsulfinyl)]butanoic acid (2.5 g) was dissolved in 10 ml water and 5 ml acetic acid followed by the addition of 5 ml 30% H2O2. The oxidation was allowed to proceed for 24 h. 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) δ1.48 (m, 2H), 1.56 (m, 2H), 1.75 (m, 2H), 2.10 (m, 2H), 2.41 (m, 2H), 2.68 (m, 2H), 3.9 (m, 1H), 4.02 (m, 2H), 7.35 (m, 9H), 7.7 (bd, 1H, J=7.9 Hz), 9.05 (bs, 2H), 9.3 (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-8f2d274b2ae141e78d49a0c94c20759d
Source dataset
uspto-grants-1995_04
Patent number
US05409939

Reaction notes

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