Acetonitrile → tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

HRID 710949Notes

Reaction equation

[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9]Br)([CH3:4])([CH3:3])[CH3:2].C(#N)C.[OH:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]>C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][O:15][N:16]1[C:20](=[O:21])[C:19]2[C:18](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]1=[O:26])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

tert-Butyl(2-bromoethyl)carbamate (5.00 g, 23.5 mmol) was stirred under an argon atmosphere at room temperature with acetonitrile (74 mL). Then, N-hydroxyphthalimide (Pht-OH, 3.83 g) and triethylamine (5.64 g) were added, followed by stirring the reaction mixture at 70° C. for 24 hours. After completion of the reaction, the reaction solution was concentrated, followed by diluting with ethyl acetate and washing with 0.5M hydrochloric acid and saturated sodium bicarbonate aqueous solution, and the organic layer was dried over magnesium sulfate, to the residue resulting from distilling off the solvent under reduced pressure was added ethyl acetate (10 ml), followed by adding hexane, thereby 4.72 g of the title compound was afforded (yield 65.7%). The instrumental data were consistent with those of the compound of Reference Example 7.

Workup

customAfter completion of the reaction
concentrationthe reaction solution was concentrated
additionby diluting with ethyl acetate
washwashing with 0.5M hydrochloric acid and saturated sodium bicarbonate aqueous solution
dry with materialthe organic layer was dried over magnesium sulfate, to the residue
customresulting
distillationfrom distilling off the solvent under reduced pressure
additionwas added ethyl acetate (10 ml)
additionby adding hexane

Sources & evidence

ORD record: ord-c84a4264df3b4b6a889c464ec1b83a28
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181250B2

Reaction notes

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