Glycine methyl ester hydrochloride → HCID 86681747, compound

HRID 571331Notes

Reaction equation

HRID 571331 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])O[C:5]2=[O:12].Cl.[NH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:5]2=[O:12]

Participants

4

Reactant 2

HCID 122755Glycine methyl ester hydrochlorideHCID 6397475-Hydroxy-1,3-dihydro-2-benzofuran-1,3-dione

Product 1

HCID 86681747HCID 86681747, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
200 °C

Procedure

In a MW vial 5-hydroxyisobenzofuran-1,3-dione (561 mg, 3.42 mmol) and methyl 2-aminoacetate hydrochloride (386 mg, 3.08 mmol) were suspended in toluene (15 ml). The obtained mixture was heated under microwave irradiation at 200° C. for 5 hours. A mixture of the desired compound with an undesired byproduct (about 1:2 ratio) was obtained. After filtration, the obtained beige solid was purified by silica gel flash chromatography (petroleum ether/EtOAc 1/1 to EtOAc) to give 7 methyl 2-(5-hydroxy-1,3-dioxoisoindolin-2-yl)acetate (78 mg, 0.332 mmol, 9.70% yield, MS/ESI+ 235.9 [MH]+).

Sources & evidence

ORD record
ord-4fa606a17c144aa786eb7a83109bf6ae
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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