Trimethylsilyl triflate → HCID 88672369, compound

HRID 342301Notes

Reaction equation

HRID 342301 reaction equation
C([O:4][C@H:5]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:7](=O)[C@H:6]1[C@H:19]([O:21][C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[CH3:20])(=O)C.[C:28]1([S:34][C:35]([O:37][Si](C)(C)C)=[CH2:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:25]([O:24][C:22]([O:21][C@@H:19]([C@@H:6]1[C@@H:7]([CH2:36][C:35]([S:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:37])[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:5]1=[O:4])[CH3:20])=[O:23])[CH:26]=[CH2:27]

Participants

6

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 11447442Silane, trimethyl[[1-(phenylthio)ethenyl]oxy]-HCID 70450099HCID 70450099, compound

Product 1

HCID 88672369HCID 88672369, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 377 mg of (3S, 4R)-4-acetoxy-3-[(R)-1-(allyloxycarbonyloxy)ethyl]-1-(p-methoxybenzyl)-2-azetidinone in 2 ml of dry methylene chloride were added 448 mg (2 mmole) of 1-phenylthio-1-(trimethylsilyloxy)ethylene and then the mixture was stirred at room temperature, A catalytic amount of trimethylsilyltrifluoromethanesulphonate was added to the mixture, which was then left to stand at room temperature overnight. The precipitate produced was dissolved in 200 ml of ethyl acetate, and the resulting solution was washed successively with 100 ml of water and 100 ml of a saturated aqueous solution of sodium chloride. It was then dried over anhydrous magnesium sulphate and subjected to Lobar column chromatography eluted with a 1:1 by volume mixture of cyclohexane and ethyl acetate, to afford 430 mg (yield 91%) of the title azetidinone.

Workup

  1. waitwas then left
  2. customThe precipitate produced
  3. washthe resulting solution was washed successively with 100 ml of water and 100 ml of a saturated aqueous solution of sodium chloride
  4. dry with materialIt was then dried over anhydrous magnesium sulphate
  5. washeluted with a 1:1 by volume mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-6ffa115e09004e3f97cddb248a87bf03
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

Loading…