Imidazole → HCID 86613240, compound

HRID 1660702Notes

Reaction equation

HRID 1660702 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C@H:5]([OH:18])[C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]([CH3:9])[CH3:8].N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C@H:5]([O:18][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11242828HCID 11242828, compound

Product 1

HCID 86613240HCID 86613240, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the crude alcohol 46 (2.2 g, 7.9 mmol) in DMF (12 mL), under argon, cooled to 0° C., imidazole (1.61 g, 23.7 mmol) and tert-butyldimethylsilyl chloride (3.57 mL, 23.7 mmol) were added. The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 18 h and diluted with Et2O (50 mL). The organic layer was separated and washed with 10% HCl (50 mL), NaHCO3 (50 mL, sat) and NaCl (50 mL, sat), dried (Na2SO4), filtered, and concentrated. The crude oil was purified by column chromatography (silica gel, EtOAc/Hexanes 1/9) to yield 47 (2.59 g, 98%) as colorless oil. Rf 0.31 (EtOAc/Hexanes 1/9). [α]D20=+5.30 (c=1, CH2Cl2). 1H-NMR (500 MHz, CDCl3): 0.07 (s, 6H), 0.84-0.91 (m, 15H), 1.42 (s, 9H), 1.98-2.01 (m, 1H), 2.43 (dd, J=6.0 and 19 Hz, 1H), 2.52 (dd, J=5.9 and 18.5 Hz, 1H), 3.47-3.48 (m, 1H), 3.65 (s, 3H), 4.17-4.19 (m, 1H), 4.41-4.44 (m, 1H). 13C-NMR (125 MHz, CDCl3): −3.6, 16.6, 17.60, 18.9, 25.7, 27.8, 28.2, 39.9, 51.5, 51.9, 59.5, 70.19, 155.9, 172.2. IR (neat) 3373.1, 2960.7, 1717.0, 1504.6, 1366.1, 1173.0, 837.0. HRMS m/z cald for C19H39NO5Si (M+Na): 390.2675 found 390.2676.

Workup

  1. waitat room temperature for 18 h
  2. customThe organic layer was separated
  3. washwashed with 10% HCl (50 mL), NaHCO3 (50 mL, sat) and NaCl (50 mL, sat)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude oil was purified by column chromatography (silica gel, EtOAc/Hexanes 1/9)

Sources & evidence

ORD record
ord-550354bf06e54c90b4dfed7ec93b68eb
Source dataset
uspto-grants-2011_10
Patent number
US08030279B2

Reaction notes

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