Tert-Butyl hypochlorite → HCID 86665546, compound

HRID 1770752Notes

Reaction equation

[CH3:1][C:2]1([CH3:128])[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][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][O:63][CH2:64][CH2:65][O:66][CH2:67][CH2:68][O:69][CH2:70][CH2:71][O:72][CH2:73][CH2:74][O:75][CH2:76][CH2:77][O:78][CH2:79][CH2:80][O:81][CH2:82][CH2:83][O:84][CH2:85][CH2:86][O:87][CH2:88][CH2:89][O:90][CH2:91][CH2:92][O:93][CH2:94][CH2:95][O:96][CH2:97][CH2:98][O:99][CH2:100][CH2:101][O:102][CH2:103][CH2:104][O:105][CH2:106][CH2:107][O:108][CH2:109][CH2:110][O:111][CH2:112][CH2:113][O:114][CH2:115][CH2:116][O:117][CH2:118][CH2:119][O:120][CH2:121][CH2:122][O:123][CH3:124])[C:5](=[O:125])[C:4]([CH3:127])([CH3:126])[NH:3]1.C(O[Cl:134])(C)(C)C>CO>[Cl:134][N:3]1[C:4]([CH3:127])([CH3:126])[C:5](=[O:125])[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][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][O:63][CH2:64][CH2:65][O:66][CH2:67][CH2:68][O:69][CH2:70][CH2:71][O:72][CH2:73][CH2:74][O:75][CH2:76][CH2:77][O:78][CH2:79][CH2:80][O:81][CH2:82][CH2:83][O:84][CH2:85][CH2:86][O:87][CH2:88][CH2:89][O:90][CH2:91][CH2:92][O:93][CH2:94][CH2:95][O:96][CH2:97][CH2:98][O:99][CH2:100][CH2:101][O:102][CH2:103][CH2:104][O:105][CH2:106][CH2:107][O:108][CH2:109][CH2:110][O:111][CH2:112][CH2:113][O:114][CH2:115][CH2:116][O:117][CH2:118][CH2:119][O:120][CH2:121][CH2:122][O:123][CH3:124])[C:2]1([CH3:128])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 2,2,5,5-tetramethyl-3-(2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86,89,92,95,98,101,104,107,110,113,116-nonatriacontaoxaoctadecahectan-118-yl)imidazolidin-4-one (1.42 g, 0.7 mmol) in methanol (150 ml) was added tert-butylhypochlorite (209 mg, 1.9 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 775 mg (54%) of the title compound. 1H NMR (400 MHz, D2O) δ 3.72 (s, 152H), 3.65 (m, 2H), 3.58 (t, J=7.5 Hz, 2H), 3.40 (s, 3H), 1.55 (s, 6H), 1.38 (s, 6H). 13C NMR (100 MHz, D2O) δ 174.9, 83.6, 71.0, 69.5 (large peak) 67.7, 66.0, 58.1, 40.2, 24.2, 22.7.

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-90ef1a48e4d64b89990ac1f06ec33959
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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