Imidazole → HCID 72485635, compound

HRID 1593655Notes

Reaction equation

HRID 1593655 reaction equation
[CH2:1]([O:8][N:9]1[C:12]2([CH:17]=[CH:16][C:15](=[O:18])[CH:14]([OH:19])[CH:13]2[OH:20])[CH2:11][C:10]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>CN(C=O)C>[CH2:1]([O:8][N:9]1[C:12]2([CH:17]=[CH:16][C:15](=[O:18])[CH:14]([O:19][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:13]2[OH:20])[CH2:11][C:10]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 69177826HCID 69177826, compound

Product 1

HCID 72485635HCID 72485635, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of rac-(4R,5S,6S)-1-benzyloxy-5,6-dihydroxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (2) (123 mg, 0.425 mmol) and imidazole (35 mg, 0.510 mmol) in DMF (0.6 ml) was added at 0° C. a solution of tert-butyldimethylsilyl chloride (77 mg, 0.510 mmol) in DMF (1.2 ml). After 12 h at room temperature, the reaction was quenched with H2O (3 ml) and the mixture extracted with AcOEt (3×5 ml). The combined extracts were washed with saturated aqueous CuSO4 solution (2×10 ml) and brine (2×10 ml), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-AcOEt, 5:2) to give rac-(4R,5S,6S)-1-benzyloxy-6-tert-butyldimethylsilyloxy-5-hydroxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (3) as a white solid (133 mg, 78%).

Workup

  1. customthe reaction was quenched with H2O (3 ml)
  2. extractionthe mixture extracted with AcOEt (3×5 ml)
  3. washThe combined extracts were washed with saturated aqueous CuSO4 solution (2×10 ml) and brine (2×10 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-AcOEt, 5:2)

Sources & evidence

ORD record
ord-3ac61dfe467b48e18195ce31ba473bb8
Source dataset
uspto-grants-2007_11
Patent number
US07297788B2

Reaction notes

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