Triethylamine → HCID 15671307, compound

HRID 1086603Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[O:12][C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15].C(N(CC)CC)C.[CH3:26][C:27]([CH3:35])([O:29][C:30]([NH:32][NH:33][CH3:34])=[O:31])[CH3:28]>O1CCCC1.CN(C1C=CN=CC=1)C>[CH3:26][C:27]([CH3:35])([O:29][C:30]([NH:32][N:33]([CH3:34])[C:14](=[O:15])[C:13]([O:12][N:3]1[C:2](=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:11])([CH3:18])[CH3:17])=[O:31])[CH3:28]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-2-methylpropanoyl chloride (5.3 g, 22 mmole) in 40 ml of dry tetrahydrofuran was treated with triethylamine (4.10 ml, 30 mmole) and 4-(N,N-dimethylamino)pyridine (5 mg). A solution of 1-[(1,1-dimethylethoxy)carbonyl]-2-methylhydrazine (2.90 g, 20 mmole) in 20 ml of tetrahydrofuran was added dropwise at 0° C. and the resulting mixture was stirred at 20° C. overnight. The solvent was evaporated and the solid residue was partitioned between ethyl acetate and water. The organic phase was washed successively with 0.5N hydrochloric acid, 5% sodium bicarbonate, and water. Drying over magnesium sulfate and evaporation gave 6.6 g of the title compound as a colorless solid, m.p. 140°-145° C.

Workup

customThe solvent was evaporated
customthe solid residue was partitioned between ethyl acetate and water
washThe organic phase was washed successively with 0.5N hydrochloric acid, 5% sodium bicarbonate, and water
dry with materialDrying over magnesium sulfate and evaporation

Sources & evidence

ORD record: ord-955c2d44dd2e4dfbb819047c98f72c76
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05030724

Reaction notes

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