Potassium Carbonate → HCID 86724825, compound

HRID 1525589Notes

Reaction equation

HRID 1525589 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C@@H:21]([CH3:35])[C@@H:22]([CH3:34])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)=[CH:16][C:15]=1[O:36][CH3:37].C(=O)([O-])[O-].[K+].[K+].[N+:44]([C:47]1[N:48]=[CH:49][NH:50][CH:51]=1)([O-:46])=[O:45]>>[CH3:33][O:32][C:26]1[CH:25]=[C:24]([CH2:23][C@H:22]([CH3:34])[C@H:21]([CH3:35])[CH2:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][N:50]3[CH:51]=[C:47]([N+:44]([O-:46])=[O:45])[N:48]=[CH:49]3)=[C:15]([O:36][CH3:37])[CH:16]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH3:31]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 86724826HCID 86724826, compoundHCID 178526856HCID 178526856, compound

Product 1

HCID 86724825HCID 86724825, compoundYield 57.3%

Procedure

The Standard Procedure 2 was followed by use of 9b (146.6 mg, 0.2512 mmol, 1.0 equiv), potassium carbonate (74.4 mg, 0.538 mmol, 2.1 equiv), and 4-nitroimidazole (6a, 56.3 mg, 0.498 mmol, 2.0 equiv). After workup and purification with column chromatography (100% EtOAc as eluant), 10c (88.4 mg, 0.144 mmol) was obtained in 57% yield as a yellow gummy oil: 1H NMR (CDCl3, 400 MHz) δ 0.81 (d, J=6.4 Hz, 3H, CH3), 0.82 (d, J=6.4 Hz, 3H, CH3), 1.73 (m, 2H, 2×CH), 2.23-2.31 (m, 2H, 2×ArCH), 2.70-2.75 (m, 2H, 2×ArCH), 3.62-3.86 (m, 21H, 3×OCH3+6×OCH2), 4.09-4.14 (m, 4H, CH2N+CH2O), 6.62-6.68 (m, 4H, 4×ArH), 6.76-6.80 (m, 2H, 2×ArH), 7.47 (s, 1H, nitroimidazole C5-H), 7.88 (s, 1H, nitroimidazole C2-H); 13C NMR (CDCl3, 100 MHz) δ 16.12, 16.18, 38.74, 38.84, 39.12, 39.21, 48.24, 55.76, 55.78, 55.85, 68.60, 69.49, 69.69, 70.54 70.57, 70.65, 110.97, 112.21, 112.81, 113.66, 120.17, 120.89, 121.04, 134.41, 135.24, 136.48, 146.18, 146.98, 147.95, 148.63, 149.22; IR (neat) 2924 (s), 2854 (s), 1634 (w), 1589 (w), 1515 (s), 1456 (m), 1417 (m), 1334 (s), 1260 (s), 1028 (s) cm−1; HRMS (FAB) m/z calcd for C32H46N3O9 (M+H)+: 616.3234. found: 616.3232.

Workup

  1. customAfter workup and purification with column chromatography (100% EtOAc as eluant)

Sources & evidence

ORD record
ord-e5f37610fcfc4f3d909085be0c7a152e
Source dataset
uspto-grants-2015_07
Patent number
US09084779B2

Reaction notes

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