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1,3-Isobenzofurandione, 5-fluoro- → Methyl 3-(5-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

HRID 10849
Notes
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Reaction equation

HRID 10849 reaction equation
[NH2:1][CH2:2][CH:3]([C:8]1([CH3:13])[O:12][CH2:11][CH2:10][O:9]1)[C:4]([O:6][CH3:7])=[O:5].[F:14][C:15]1[CH:16]=[C:17]2[C:22](=O)[O:21][C:19](=[O:20])[C:18]2=[CH:24][CH:25]=1>>[F:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:24][CH:25]=1)[C:19](=[O:20])[N:1]([CH2:2][CH:3]([C:8]1([CH3:13])[O:9][CH2:10][CH2:11][O:12]1)[C:4]([O:6][CH3:7])=[O:5])[C:22]2=[O:21]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 675721,3-Isobenzofurandione, 5-fluoro-HCID 21982209Methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

Product 1

HCID 21982231Methyl 3-(5-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

Procedure

Methyl 3-(5-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.66 g, 47%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.80 g, 5.07 mmol) and 4-fluorophthalic anhydride (0.80 g, 5.07 mmol), and the obtained product was identified with the following NMR data.

Sources & evidence

ORD record
ord-128369000365468e8ac4191f5ff6d728
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094908B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes