Imidazole → HCID 54163843, compound

HRID 1090334Notes

Reaction equation

HRID 1090334 reaction equation
[CH2:1]([N:8]1[CH:11]([C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH2:13])[CH:10]([CH:18]([O:20]C(OCC2C=CC=CC=2)=O)[CH3:19])[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.N1C=CN=C1.[Si:42](Cl)([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43]>CO.[Pd]>[CH2:1]([N:8]1[CH:11]([CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH3:13])[CH:10]([CH:18]([O:20][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH3:19])[C:9]1=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 19915058HCID 19915058, compound

Product 1

HCID 54163843HCID 54163843, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 28 mg (0.07 mmol) of 1-benzyl-3-(1-benzyloxycarbonyloxyethyl)-4-(1-methoxycarbonylethenyl)-2-azetidinone dissolved in 2 ml of methanol, 5 mg of 5% palladium charcoal was added and the mixture was stirred under hydrogen atmosphere for a night. The reaction solution was filtered with selite and the filtrate was washed with ethyl acetate and concentrated. To the concentrate were added 1 ml of DMF, 20 mg (0.3 mmol) of imidazole and 45 mg (0.3 mmol) of t-butyldimethylsilylchloride and the mixture was stirred for a night. Ice water was added to the reaction solution and the resultant was extracted with ether, washed with a saturated solution of NaCl, dried with magnesium sulfate, concentrated and purified with 2 g of silica-gel column (hexane:ether 1:1) to give 22 mg of 1-benzyl-4-(1-methoxycarbonylethyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone (yield: 84%). Comparison with the NMR data showed α:β=1:1.

Workup

  1. filtrationThe reaction solution was filtered with selite
  2. washthe filtrate was washed with ethyl acetate
  3. concentrationconcentrated
  4. stirringthe mixture was stirred for a night
  5. extractionthe resultant was extracted with ether
  6. washwashed with a saturated solution of NaCl
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated
  9. custompurified with 2 g of silica-gel column (hexane:ether 1:1)

Sources & evidence

ORD record
ord-001d270595c247b9b02f30d8e3e3092c
Source dataset
uspto-grants-1992_01
Patent number
US05081238

Reaction notes

Loading…