Beta-Alanine → 3-Phthalimidopropionic acid

HRID 717346Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[C:7]1(=O)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[O:8]1.C([O-])(=O)C.[K+]>C(O)(=O)C.C(OCC)(=O)C>[O:8]=[C:7]1[C:11]2[C:10](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9](=[O:16])[N:1]1[CH2:2][CH2:3][C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

Into a 3-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-aminopropanoic acid (20 g, 224.48 mmol, 1.00 equiv) and 1,3-dihydro-2-benzofuran-1,3-dione (33.28 g, 224.69 mmol, 1.00 equiv) in acetic acid (1,200 mL). This was followed by the addition of potassium acetate (66.0 g, 672.49 mmol, 3.00 equiv) in several batches at 0° C. The resulting solution was stirred for 3 h at 80° C. in an oil bath. The resulting mixture was concentrated under vacuum. The reaction was then quenched by the addition of 150 mL of water. The solids were collected by filtration. This resulted in 40 g (81%) of 3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanoic acid as a white solid. Rf: 0.15 (in ethyl acetate:petroleum ether=1:1).

Workup

customInto a 3-L 4-necked round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
concentrationThe resulting mixture was concentrated under vacuum
customThe reaction was then quenched by the addition of 150 mL of water
filtrationThe solids were collected by filtration
customThis resulted in 40 g (81%) of 3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanoic acid as a white solid

Sources & evidence

ORD record: ord-27ecbc891b4e4747bef677d8508bff9d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193707B2

Reaction notes

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