p-Toluenesulfonic acid monohydrate → HCID 21982260, compound

HRID 10887Notes

Reaction equation

HRID 10887 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:27])[N:7]([CH2:14][CH:15]([C:21]1([CH3:26])OCC[O:22]1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2=[O:13])([O-:3])=[O:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:27])[N:7]([CH2:14][CH:15]([C:21](=[O:22])[CH3:26])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2=[O:13])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21982203Ethyl 3-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

Product 1

HCID 21982260HCID 21982260, compound

Procedure

Ethyl 2-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (116 mg, 22%) in the same manner as described in the above example 6 (20) from ethyl 3-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.38 g, 1.58 mmol) and p-toluenesulfonic acid monohydrate (25 mg), and the obtained product was identified with the following NMR data.

Sources & evidence

ORD record
ord-b32310baa350497fbb1d64d219987896
Source dataset
uspto-grants-2006_08
Patent number
US07094908B2

Reaction notes

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