Imidazole → HCID 21034347, compound

HRID 1830944Notes

Reaction equation

HRID 1830944 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:9][O:10][C:11]1[C:16]2[C:17](=[O:27])[N:18]3[CH2:25][C@H:24]([OH:26])[CH2:23][C@H:19]3[C:20](=[O:22])[NH:21][C:15]=2[CH:14]=[CH:13][C:12]=1[O:28][CH3:29].N1C=CN=C1.O>CN(C=O)C>[CH3:9][O:10][C:11]1[C:16]2[C:17](=[O:27])[N:18]3[CH2:25][C@H:24]([O:26][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:23][C@H:19]3[C:20](=[O:22])[NH:21][C:15]=2[CH:14]=[CH:13][C:12]=1[O:28][CH3:29]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 23574467HCID 23574467, compound

Product 1

HCID 21034347HCID 21034347, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solid TBDMS Chloride (8.22 g, 54.44 mmol) was added in one portion to a solution of 170 (7.23 g, 24.74 mmol) and imidazole (8.42 g, 123.72 mmol) in anhydrous DMF (75 mL) and allowed to stir at room temperature for 16 h. The reaction mixture was poured into water (500 mL) and filtered to afford the crude product (171), which was purified by recrystallisation from EtOH (800 mL) as fine white needles (6.995 g, 17.21 mmol, 70%). 1H NMR (270 MHz, CDCl3) δ10.06 (s, 1H, NH), 7.37 (s, 1H, ArH), 6.68 (s, 1H, ArH), 4.19-4.14 (m, 1H, 2), 4.06-4.01 (m, 1H, 11a), 3.90 (s, 3H, OMe), 3.88 (s, 3H, OMe), 3.69-3.63 (m, 2H, 3), 2.85-2.80 (m, 1H, 1), 2.05-2.01 (m, 1H, 1); 13C NMR (67.8 MHz, CDCl3) δ170.4, 170.2, 165.9, 152.1, 145.8, 145.6, 131.1, 130.7, 118.1, 111.9, 104.3, 104.1, 69.2, 69.1, 56.0, 55.9, 55.7, 54.3, 54.0, 35.0, 25.8, 25.7, 25.6, 17.9, −3.0, −3.5, −4.9, −5.0.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-a05246b83693429abc170db0ceedcf41
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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