Sodium Methoxide → HCID 86724823, compound

HRID 1525587Notes

Reaction equation

HRID 1525587 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@@H:12]([CH3:26])[C@@H:13]([CH3:25])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)=[CH:7][C:6]=1[O:27][CH3:28].C[O-].[Na+].[N+:32]([C:35]1[N:36]=[CH:37][NH:38][CH:39]=1)([O-:34])=[O:33]>>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([CH2:14][C@H:13]([CH3:25])[C@H:12]([CH3:26])[CH2:11][C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:38]3[CH:39]=[C:35]([N+:32]([O-:34])=[O:33])[N:36]=[CH:37]3)=[C:6]([O:27][CH3:28])[CH:7]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

4

Reactant 3

HCID 10942334Sodium MethoxideHCID 86724824HCID 86724824, compoundHCID 178526856HCID 178526856, compound

Product 1

HCID 86724823HCID 86724823, compoundYield 65%

Procedure

The Standard Procedure 2 was followed by use of 9a (72.2 mg, 0.160 mmol, 1.0 equiv), sodium methoxide (19.1 mg, 0.353 mmol, 2.2 equiv), and 4-nitroimidazole (6a, 36.3 mg, 0.321 mmol, 2.0 equiv). After workup and purification with column chromatography (80% EtOAc in hexanes as eluant), 10a (50.3 mg, 0.104 mmol) was obtained in 65% yield as white solids: mp (recrystallized from methanol) 98.3-98.8° C.; 1H NMR (CDCl3, 400 MHz) δ 0.80 (d, J=6.8 Hz, 3H, CH3), 0.83 (d, J=6.8 Hz, 3H, CH3), 1.74 (m, 2H, 2×CH), 2.22-2.34 (m, 2H, 2×ArCH), 2.69-2.76 (m, 2H, 2×ArCH), 3.81 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 4.25 (t, J=4.8 Hz, 2H, CH2N), 4.37 (t, J=4.8 Hz, 2H, CH2O), 6.62-6.68 (m, 4H, 4×ArH), 6.71-6.78 (m, 2H, 2×ArH), 7.60 (d, J=1.4 Hz, 1H, nitroimidazole C5-H), 8.13 (d, J=1.4 Hz, 1H, nitroimidazole C2-H); 13C NMR (CDCl3, 100 MHz) δ 16.03, 16.16, 38.70, 38.93, 39.06, 39.25, 47.92, 55.61, 55.73, 55.82, 68.38, 110.98, 112.23, 112.78, 114.90, 120.62, 120.85, 120.93, 134.26, 136.55, 137.02, 144.90, 146.99, 147.98, 148.61, 149.66; IR (neat) 2957 (s), 2933 (s), 1590 (w), 1543 (s), 1516 (m), 1456 (w), 1337 (s), 1262 (m), 1235 (s), 1031 (s) cm−1; HRMS (FAB) m/z calcd for C26H34N3O6 (M+H)+: 484.2448. found: 484.2444.

Workup

  1. customAfter workup and purification with column chromatography (80% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-e02a66b85fe1447f9589826fd0af156c
Source dataset
uspto-grants-2015_07
Patent number
US09084779B2

Reaction notes

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