Pyridine → HCID 54479352, compound

HRID 863654Notes

Reaction equation

HRID 863654 reaction equation
[C:1]([O:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11](=[O:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.[C:26]([Si:30]([CH3:33])([CH3:32])Cl)([CH3:29])([CH3:28])[CH3:27].P([O-])([O-])([O-])=O>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:4][C@@H:5]1[N:8]([Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:33])[CH3:32])[C:7](=[O:9])[C@H:6]1[NH:10][C:11](=[O:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 1061PhosphateHCID 28928tert-Butyldimethylsilyl chlorideHCID 10923331HCID 10923331, compound

Product 1

HCID 54479352HCID 54479352, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.5 g of (3S,4S)-4-acetoxy-3-phenylacetamido-azetidin-2-one in 100 ml of dichloromethane, at room temperature and under inert atmosphere, 0.069 g (0.56 moles) of 4-dimethylamino pyridine and 0.5 ml of pyridine are added. To this mixture 0.907 g (6 mmoles) of tert-butyldimethylchlorosilane dissolved in 10 ml of anhydrous dichloromethane are slowly added. The mixture is let under stirring for about 24 hours, then a phosphate buffer at pH 7.5 is added. The organic phase is extracted with dichloromethane and the dichloromethane phase is washed with a saturated solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under vacuum. Thus, essentially pure (3S,4S)-4-acetoxy-3-phenylacetamido-1-tert-butyldimethylsilyl-azetidin-2-one (III, R=TBDMS) is obtained in quantitative yield.

Workup

  1. additionare slowly added
  2. extractionThe organic phase is extracted with dichloromethane
  3. washthe dichloromethane phase is washed with a saturated solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e60d9e82e1d545b8867097faa3b64166
Source dataset
uspto-grants-1998_02
Patent number
US05721360

Reaction notes

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