p-Toluenesulfonic acid monohydrate → Allyl 2-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate

HRID 10900Notes

Reaction equation

HRID 10900 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4](=[O:27])[N:5]([CH2:13][CH:14]([C:21]1([CH3:26])OCC[O:22]1)[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[C:6]2=[O:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]2[C:7]=1[C:6](=[O:12])[N:5]([CH2:13][CH:14]([C:21](=[O:22])[CH3:26])[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[C:4]2=[O:27]

Participants

3

Procedure

Allyl 2-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (86 mg, 23%) in the same manner as described in the above Example 6 (40) from allyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.35 g, 0.92 mmol) and p-toluenesulfonic acid monohydrate (40 mg), and the obtained product was identified with the following NMR data.

Sources & evidence

ORD record
ord-e0e06be6c1f349d980d1a243c257c9be
Source dataset
uspto-grants-2006_08
Patent number
US07094908B2

Reaction notes

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