Imidazole → HCID 131732055, compound

HRID 338557Notes

Reaction equation

HRID 338557 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[N:12]([C@H:15]1[C@@H:21]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:20][CH:18]([OH:19])[C@H:17]([OH:31])[C@H:16]1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[N+:13]=[N-:14].N1C=CN=C1>CN(C)C1C=CN=CC=1.CN(C)C=O>[N:12]([C@H:15]1[C@@H:21]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:20][C@@H:18]([O:19][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])[C@H:17]([OH:31])[C@H:16]1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[N+:13]=[N-:14]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 131729985HCID 131729985, compound

Product 1

HCID 131732055HCID 131732055, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Triisopropylsilyl chloride (0.63 mL, 3.0 mmol, 1.2 equiv) was added to a solution of hemiacetal 223 (0.959 g, 2.49 mmol, 1.00 equiv), imidazole (0.409 g, 6.01 mmol, 2.41 equiv), and 4-dimethylaminopyridine (29 mg, 0.24 mmol, 0.096 equiv) in dimethylformamide (2.5 mL). After 19 h, the yellow solution was concentrated and purified by silica gel chromatography (hexane/ethyl acetate 19:1 to 9:1) to afford 224 (0.800 g, 1.48 mmol, 59% yield) as a colorless oil. Rf=0.49 (hexane/ethyl acetate 4:1); 1H NMR (500 MHz, CDCl3) δ 7.43-7.24 (m, 10H), 4.78 (d, J=11.8, 1H), 4.75 (d, J=11.8, 1H), 4.55 (d, J=11.6, 1H), 4.52 (d, J=12.0, 1H), 4.51 (d, J=7.3, 1H), 3.98 (d, J=3.6, 1H), 3.72 (ddd, J=9.5, 7.3, 2.1, 1H), 3.69-3.58 (m, 3H), 3.56 (dd, J=9.6, 3.7, 1H), 2.26 (d, J=2.2, 1H), 1.19-0.99 (m, 21H); 13C NMR (126 MHz, CDCl3) δ 137.86, 137.84, 128.70, 128.63, 128.08, 128.05, 127.97, 127.93, 98.09, 80.69, 73.81, 73.78, 72.80, 72.01, 68.83, 59.83, 17.96, 17.90, 12.33; FTIR (neat film) 3463.8, 2943.4, 2866.2, 2108.6, 1455.3, 1366.1, 1280.0, 1185.4, 1099.0, 1028.7, 1014.6, 997.6, 883.5, 805.4, 736.3, 695.5, 669.0 cm−1; HRMS (ESI) m/z: Calcd for C29H43N3O5SiNa (M+Na+) 564.2870. found 564.2870.

Workup

  1. concentrationthe yellow solution was concentrated
  2. custompurified by silica gel chromatography (hexane/ethyl acetate 19:1 to 9:1)

Sources & evidence

ORD record
ord-4f1e9a40338345f1b506d70a7e2b2dd4
Source dataset
uspto-grants-2014_11
Patent number
US08889842B2

Reaction notes

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