3,6-Difluorophthalic anhydride → Methyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

HRID 10839Notes

Reaction equation

HRID 10839 reaction equation
O=C1C2CCCCC=2C(=O)N1CC(C1(C)OCCO1)C(OC)=O.[NH2:24][CH2:25][CH:26]([C:31]1([CH3:36])[O:35][CH2:34][CH2:33][O:32]1)[C:27]([O:29][CH3:30])=[O:28].[F:37][C:38]1[CH:48]=[CH:47][C:46]([F:49])=[C:40]2[C:41]([O:43][C:44](=O)[C:39]=12)=[O:42]>>[F:37][C:38]1[CH:48]=[CH:47][C:46]([F:49])=[C:40]2[C:39]=1[C:44](=[O:43])[N:24]([CH2:25][CH:26]([C:31]1([CH3:36])[O:32][CH2:33][CH2:34][O:35]1)[C:27]([O:29][CH3:30])=[O:28])[C:41]2=[O:42]

Participants

4

Reactant 3

HCID 5139183,6-Difluorophthalic anhydrideHCID 21982186HCID 21982186, compoundHCID 21982209Methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

Product 1

HCID 21982183Methyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

Procedure

Methyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.27 g, 31%) 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 (0.47 g, 2.47 mmol) and 3,6-difluorophthalic anhydride (0.50 g, 2.72 mmol), and the obtained product was identified with the following NMR data.

Sources & evidence

ORD record
ord-55e268810b43421a99d2245b5297b31f
Source dataset
uspto-grants-2006_08
Patent number
US07094908B2

Reaction notes

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