p-Toluenesulfonic acid monohydrate → HCID 21982222, compound

HRID 10874Notes

Reaction equation

HRID 10874 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][CH:15]([C:20]1([CH3:25])OCC[O:21]1)[C:16]([O:18][CH3:19])=[O:17])[C:7]2=[O:26])([O-:3])=[O:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][CH:15]([C:20](=[O:21])[CH3:25])[C:16]([O:18][CH3:19])=[O:17])[C:7]2=[O:26])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21982205Methyl 3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

Product 1

HCID 21982222HCID 21982222, compound

Procedure

Methyl 2-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (95 mg, 35%) in the same manner as described in the above example 6 (1) from methyl 3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.29 g, 0.82 mmol) and p-toluenesulfonic acid monohydrate (50 mg), and the obtained product was identified with the following NMR data.

Sources & evidence

ORD record
ord-a9eb773d5cf146d1882af8f7a3cef232
Source dataset
uspto-grants-2006_08
Patent number
US07094908B2

Reaction notes

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