Tert-Butyl hypochlorite → HCID 86665552, compound

HRID 1770771Notes

Reaction equation

[CH3:1][C:2]1([CH3:53])[N:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH3:49])[C:5](=[O:50])[C:4]([CH3:52])([CH3:51])[NH:3]1.C(O[Cl:59])(C)(C)C>CO>[Cl:59][N:3]1[C:4]([CH3:52])([CH3:51])[C:5](=[O:50])[N:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH3:49])[C:2]1([CH3:53])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 2,2,5,5-tetramethyl-3-(2,5,8,11,14,17,20,23,26,29,32,35,38,41-tetradecaoxatritetracontan-43-yl)imidazolidin-4-one (1.13 g, 1.2 mmol) in methanol (150 ml) was added tert-butylhypochlorite (393 mg, 3.6 mmol). The mixture was stirred for 1 hour at 0° C. The reaction mixture was concentrated in vacuo, and crude material is purified by silica gel flash chromatography (0 to 10% methanol in dichloromethane) to give 764 mg (66%) of the title compound. 1H NMR (400 MHz, D2O) δ 3.70 (s, 54H), 3.64 (m, 2H), 3.56 (t, J=7.5 Hz, 2H), 3.39 (s, 3H), 1.54 (s, 6H), 1.37 (s, 6H). 13C NMR (100 MHz, D2O) δ 175.0, 83.6, 71.0, 69.4 (large peak), 67.7, 66.0, 58.0, 40.2, 24.1, 22.6.

Workup

concentrationThe reaction mixture was concentrated in vacuo, and crude material
customis purified by silica gel flash chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-8b9c7fff38b6462b9a0ccafe437e4372
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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