Tert-Butyl hypochlorite → HCID 86665543, compound

HRID 1770751Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][C:13]1([CH3:34])[CH2:17][N:16]([CH2:18][CH2:19][N+:20]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])([CH3:22])[CH3:21])[C:15](=[O:33])[NH:14]1.C(O[Cl:40])(C)(C)C>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[Cl:40][N:14]1[C:13]([CH3:34])([CH3:12])[CH2:17][N:16]([CH2:18][CH2:19][N+:20]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])([CH3:22])[CH3:21])[C:15]1=[O:33]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N,N-dimethylethanaminium 4-methylbenzenesulfonate (162 mg, 0.32 mmol) in methanol (1 ml) was cooled to 0° C. tert-Butylhypochlorite (45 ul, 0.4 mmol) was added. The resulting solution was stirred for 2 hours at 0° C. and then concentrated under reduced pressure. The residue was purified by reverse phase HPLC eluting from a C18 column with a gradient of 5 to 95% CH3CN in water (with 0.01% acetic acid) to give 75 mg of a clear oil. 1H NMR (D2O, 400 MHz) δ 1.21 (s, 6H), 2.29 (s, 3H), 3.09 (s, 6H) 3.26 (s, 3H), 3.31 (s, 2H), 3.48-3.36 (m, 14H), 3.84 (br m, 2H), 7.25-7.27 (d, J=8.1 Hz, 2H), 7.58-7.60 (d, J=8.2 Hz, 2H). 13C NMR (D2O, 100 MHz) δ 161.2, 142.4, 139.6, 129.4, 125.3, 70.9, 69.7, 69.4, 69.4, 63.9, 63.6, 62.4, 61.1, 58.0, 55.5, 51.8, 38.9, 22.3, 20.5; LRMS (ESI/APCI) m/z 366 [M]+.

Workup

additionwas added
concentrationconcentrated under reduced pressure
customThe residue was purified by reverse phase HPLC
washeluting from a C18 column with a gradient of 5 to 95% CH3CN in water (with 0.01% acetic acid)

Sources & evidence

ORD record: ord-1222ea481a97490395a9af7ae4be2324
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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