Imidazole → HCID 68634095, compound

HRID 1799451Notes

Reaction equation

HRID 1799451 reaction equation
[OH:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[CH:4]([CH2:5][C@@H:6]([OH:29])[C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.N1C=CN=C1.[CH3:35][C:36]([Si:39](Cl)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([CH3:38])[CH3:37]>CN(C=O)C>[Si:39]([O:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[CH:4]([CH2:5][C@@H:6]([OH:29])[C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1)([C:36]([CH3:38])([CH3:37])[CH3:35])([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 22809921HCID 22809921, compound

Product 1

HCID 68634095HCID 68634095, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 25 (950 mg, 2.34 mmol) and imidazole (396 mg, 5.81 mmol) was dissolved in 5 mL of DMF. TBDPSCl (0.74 mL, 2.79 mmol) was added to the solution dropwise over a 30 min-period using a syringe. The reaction was stirred at room temperature for 16 h. The crude product was chromatographed (SiO2, gradient, hexane/EtOAc 10:1 to 5:1) to give 1.37 g (2.12 mmol, 91%) of 56 which was slightly contaminated with TBDPSCl. Rf 0.46 (hexane/EtOAc 5:1); 1H NMR (400 MHz, CDCl3) δ 7.68 (m, 4H, H-2 of phenyl), 7.43-7.32 (m, 6H, H-3 and H-4 of phenyl), 3.82 (m, 1H, H-3/H-7), 3.67 (s, 3H, CO2CH3), 3.46 (m, 1H, H-3/H-7), 2.40-0.69 (m, 28H), 1.04 (s, 9H, C(CH3)3), 0.93 (d, 3H, J=6.4 Hz, CH3), 0.79 (s, 3H, CH3), 0.64 (s, 3H, CH3); MS (ESI) Calcd for C41H60O4SiNa (M+Na+): 667.4. Found: 667.4.

Workup

  1. customThe crude product was chromatographed (SiO2, gradient, hexane/EtOAc 10:1 to 5:1)

Sources & evidence

ORD record
ord-3f43d103256148188877a467b7c2ba58
Source dataset
uspto-grants-2013_01
Patent number
US08344125B2

Reaction notes

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