Imidazole → HCID 131716748, compound

HRID 703405Notes

Reaction equation

HRID 703405 reaction equation
[CH2:1]([C@H:3]1[C@@H:6]([CH2:7][OH:8])[NH:5][C:4]1=[O:9])[CH3:2].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C)C=O>[CH2:1]([C@H:3]1[C@@H:6]([CH2:7][O:8][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[NH:5][C:4]1=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 131716749HCID 131716749, compound

Product 1

HCID 131716748HCID 131716748, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

187 mg of (±)-cis-3-ethyl-4-hydroxymethyl-2-azetidinone, 300 mg of imidazole, and 300 mg of t-butyldimethylsilyl chloride in 3 ml dry dimethylformamide (DMF) were stirred at room temperature for 2 hours. The mixture was concentrated to dryness and 25 ml of H2O:EtOAc (2:3) were added. The mixture was washed 3 times with 3 ml of H2O to remove DMF and imidazole and then dried over Na2SO4 and concentrated to yield the titled compound as white crystals. NMR (CDCl3): δ0.06 (6H, s), 0.89 (9H, s), 1.06 (3H, t), 1.48-1.88 (2H, m), 3.14 (1H, m), 3.56-3.90 (3H, m), 5.86 (1H, brs).

Workup

  1. concentrationThe mixture was concentrated to dryness and 25 ml of H2O:EtOAc (2:3)
  2. additionwere added
  3. washThe mixture was washed 3 times with 3 ml of H2O
  4. customto remove DMF and imidazole
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-88848279d2b44c1e91ff8725e73b399a
Source dataset
uspto-grants-1991_01
Patent number
US04983597

Reaction notes

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