Tert-Butyl hypochlorite → HCID 56966377, compound

HRID 1770760Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[O:7][C:6](=[O:8])[NH:5][C:4]1([CH3:10])[CH3:9].[Cl:11]OC(C)(C)C>CO>[Cl:11][N:5]1[C:4]([CH3:10])([CH3:9])[CH:3]([CH2:2][OH:1])[O:7][C:6]1=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 5-(hydroxymethyl)-4,4-dimethyloxazolidin-2-one (250 mg, 1.72 mmol) in 2 mL of methanol was added tertbutyl hypochlorite (290 uL, 2.58 mmol). The reaction was stirred at 0° C. for 1 hour, then concentrated to a crude residue under reduced pressure. The crude product was purified by column chromatography (20 to 80% ethyl acetate in hexanes) to give the title compound as a clear liquid (248 mg, 1.38 mmol, 80%). 1H NMR (CDCl3, 400 MHz) δ 1.29 (s, 3H), 1.42 (s, 3H), 2.28-2.31 (dd, J=4.8, 7.7 1H), 3.85-3.88 (m, 1H), 3.91-3.98 (m, 1H), 4.37-4.40 (dd, J=4.7 6.9 Hz, 1H). LRMS (ESI/APCI) m/z 180 [M+H]+.

Workup

concentrationconcentrated to a crude residue under reduced pressure
customThe crude product was purified by column chromatography (20 to 80% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-1b41be72681b4dc391c47b26ac914dfd
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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