p-Toluenesulfonic acid monohydrate → HCID 21982236, compound

HRID 10897Notes

Reaction equation

HRID 10897 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH:13]([C:19]1([CH3:24])OCC[O:20]1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2=[O:25].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH:13]([C:19](=[O:20])[CH3:24])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2=[O:25]

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21982194Ethyl 3-(5-bromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

Product 1

HCID 21982236HCID 21982236, compound

Procedure

Ethyl 2-(5-bromo-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (168 mg, 31%) in the same manner as described in the above example 6 (20) from ethyl 3-(5-bromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.41 g, 1.36 mmol) and p-toluenesulfonic acid monohydrate (50 mg), and the obtained product was identified with the following NMR data.

Sources & evidence

ORD record
ord-e70fee253b1a44369d949e92a133e2c0
Source dataset
uspto-grants-2006_08
Patent number
US07094908B2

Reaction notes

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