Imidazole → HCID 69551805, compound

HRID 984540Notes

Reaction equation

HRID 984540 reaction equation
[CH3:1][O:2][C:3](=[O:46])[CH2:4][CH:5]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[C:6]([CH3:37])([CH3:36])[C:7](=[O:35])[CH:8]([CH3:34])[CH:9]([OH:33])[CH:10]([CH3:32])[CH2:11][CH2:12][CH2:13][C:14]([CH3:31])=[CH:15][CH2:16][CH:17]([O:27][C:28](=[O:30])[CH3:29])[C:18]([CH3:26])=[CH:19][C:20]1[N:21]=[C:22]([CH3:25])[S:23][CH:24]=1.N1C=CN=C1.[CH2:52]([Si:54](Cl)([CH2:57][CH3:58])[CH2:55][CH3:56])[CH3:53]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:46])[CH2:4][CH:5]([O:38][Si:39]([C:42]([CH3:44])([CH3:43])[CH3:45])([CH3:41])[CH3:40])[C:6]([CH3:36])([CH3:37])[C:7](=[O:35])[CH:8]([CH3:34])[CH:9]([O:33][Si:54]([CH2:57][CH3:58])([CH2:55][CH3:56])[CH2:52][CH3:53])[CH:10]([CH3:32])[CH2:11][CH2:12][CH2:13][C:14]([CH3:31])=[CH:15][CH2:16][CH:17]([O:27][C:28](=[O:30])[CH3:29])[C:18]([CH3:26])=[CH:19][C:20]1[N:21]=[C:22]([CH3:25])[S:23][CH:24]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 69552354HCID 69552354, compound

Product 1

HCID 69551805HCID 69551805, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 115 mg (0.17 mmol) 15-acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid methyl ester (289) and 36 mg (0.50 mmol) imidazole in 1000 μl absolute DMF was cooled to 0° C. After addition of 84 μl (0.50 mmol) triethylsilylchloride, the icebath was removed and the solution was stirred for 3 h 15 min at ambient temperature before 5.0 mL diethylether were added. The organic layer was washed with demi water (2×1000 μl) as well as with brine (1×1000 μl), dried over Na2SO4, filtrated and concentrated in vacuo. The remaining oil was purified via flash chromatography (column dimensions: 1.0×20.0 cm, diethylether/petroleum ether=1:1).

Workup

  1. customthe icebath was removed
  2. additionwere added
  3. washThe organic layer was washed with demi water (2×1000 μl) as well as with brine (1×1000 μl)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe remaining oil was purified via flash chromatography (column dimensions: 1.0×20.0 cm, diethylether/petroleum ether=1:1)

Sources & evidence

ORD record
ord-1e9dfa8fd6674260821262101340c659
Source dataset
uspto-grants-2005_03
Patent number
US06867333B2

Reaction notes

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