Imidazole → HCID 54008124, compound

HRID 1588114Notes

Reaction equation

HRID 1588114 reaction equation
[CH2:1]([O:4][C@H:5]1[C@@H:20]([OH:21])[C@@H:19]([CH2:22][OH:23])[O:18][C@@H:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C@@H:6]1[OH:24])[CH:2]=[CH2:3].N1C=CN=C1.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].CO>CN(C)C=O>[CH2:1]([O:4][C@H:5]1[C@@H:20]([OH:21])[C@@H:19]([CH:22]([Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[OH:23])[O:18][C@@H:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C@@H:6]1[OH:24])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 887MethanolHCID 28928tert-Butyldimethylsilyl chloride2×HCID 54336104HCID 54336104, compound

Product 1

HCID 54008124HCID 54008124, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 2 of Example 2 (10.85 g) was dissolved in dry dimethylformamide (DMF, 120 mL) containing imidazole (1.63 g) and 4 Å molecular sieves and cooled in an ice bath. To this, t-butyldimethylsilyl chloride (tBDMS chloride, 3.6 g) was added and stirred at this temperature for 10 min and then at room temperature 1 h. Another portion of imidazole (1.05 g) and tBDMS chloride (2.34 g) were added to the ice cold solution and stirred for 1 h. Methanol (1 mL) was added and the reaction mixture was evaporated to dryness. The residue was dissolved in CH2Cl2 and washed with water, 1M ice cold HCl and saturated NaHCO3 solution. The solution was dried over anhydrous magnesium sulfate, filtered and evaporated. 1H n.m.r. of the crude product (12.0 g of colorless solid) showed it to be essentially pure titled compound. [α]D25 -3.2±2° (c 1.03, CHCl3). 1H n.m.r.(CDCl3 +D2O<5%) ∂: 5.95 (m, 1 H, --CH=C), 5.33 and 5.23 (m, 2 H, C=CH2), 4.24 (m, 3 H, H-1, J1,2 =Hz, O--CH2 --C=), 4.06 (d, H-4), 3.9-3.8 (m, 3 H, H-6a,b, OCH2 --C), 3.73 (dd, H-2), 3.67 (s, COOCH3), 3.52 (m, OCH2 --C), 3.44 (m, H-5), 3.35 (dd, H-3),2.32 (t, CH2COO), 1.65 and 1.40 (6 H, hydrogens of pentyl group), 0.89 (s, t-butyl group), 0.09 (d, CH3 --Si--CH3). 13C n.m.r. (CDCl3) ∂: 173.9, 134.8, 117.4, 103.2, 80.7, 75.0, 71.2, 71.0, 69.3, 66.3, 62.2, 51.3, 33.9, 29.2, 25.9, 25.6, 24.6, 18.3, -5.34, -5.39. Anal. Calcd for C22H2842O8Si: C, 57.14; H, 9.09. Found: C, 56.30; H 9.06.

Workup

  1. temperaturecooled in an ice bath
  2. customat room temperature
  3. custom1 h
  4. stirringstirred for 1 h
  5. customthe reaction mixture was evaporated to dryness
  6. dissolutionThe residue was dissolved in CH2Cl2
  7. washwashed with water, 1M ice cold HCl and saturated NaHCO3 solution
  8. dry with materialThe solution was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-075f1a6719854868b528502633a83794
Source dataset
uspto-grants-1993_06
Patent number
US05220008

Reaction notes

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