Potassium Carbonate → HCID 86724820, compound

HRID 1525585Notes

Reaction equation

HRID 1525585 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:15]=[C:16]([CH2:22][C@@H:23]([CH3:37])[C@@H:24]([CH3:36])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].[N+:44]([C:47]1[N:48]=[CH:49][NH:50][CH:51]=1)([O-:46])=[O:45]>>[CH3:35][O:34][C:28]1[CH:27]=[C:26]([CH2:25][C@H:24]([CH3:36])[C@H:23]([CH3:37])[CH2:22][C:16]2[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[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)[CH:15]=2)[CH:31]=[CH:30][C:29]=1[O:32][CH3:33]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 86724821HCID 86724821, compoundHCID 178526856HCID 178526856, compound

Product 1

HCID 86724820HCID 86724820, compoundYield 88%

Procedure

The Standard Procedure 2 was followed by use of 5b (130.8 mg, 0.2241 mmol, 1.0 equiv), potassium carbonate (63.6 mg, 0.460 mmol, 2.1 equiv), and 4-nitroimidazole (6a, 50.2 mg, 0.444 mmol, 2.0 equiv). After workup and purification with column chromatography (100% EtOAc as eluant), 7c (121.3 mg, 0.1971 mmol) was obtained in 88% yield as a yellow gummy oil: 1H NMR (CDCl3, 400 MHz) δ 0.80 (d, J=6.0 Hz, 6H, 2×CH3), 1.71-1.72 (m, 2H, 2×CH), 2.22-2.28 (m, 2H, 2×ArCH), 2.69-2.73 (m, 2H, 2×ArCH), 3.61-3.85 (m, 21H, 3×OCH3+6×OCH2), 4.08-4.12 (m, 4H, CH2N+CH2O), 6.61 (s, 1H, ArH), 6.65-6.68 (m, 3H, 3×ArH), 6.74-6.77 (m, 2H, 2×ArH), 7.46 (d, J=1.0 Hz, 1H, nitroimidazole C5-H), 7.87 (d, J=1.0 Hz, 1H, nitroimidazole C2-H); 13C NMR (CDCl3, 100 MHz) δ 15.97, 16.00, 38.54, 38.59, 39.01, 39.04, 48.02, 55.59, 55.69, 55.77, 68.26, 69.30, 69.49, 70.32, 70.37, 70.40, 70.49, 110.87, 111.58, 112.07, 114.57, 120.17, 120.77, 121.47, 134.30, 134.40, 136.45, 146.80, 147.33, 147.69, 147.76, 148.48; IR (neat) 2924 (s), 2868 (s), 1607 (w), 1589 (w), 1516 (s), 1456 (m), 1335 (s), 1260 (s), 1236 (s), 1028 (s) cm−1; HRMS (FAB) m/z calcd for C32H46N3O9 (M+H)+: 616.3234. found: 616.3239.

Workup

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

Sources & evidence

ORD record
ord-c4a55a981bff4e218700b5afd14bec8f
Source dataset
uspto-grants-2015_07
Patent number
US09084779B2

Reaction notes

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