Hydroquinone → HCID 86747601, compound

HRID 1975463Notes

Reaction equation

HRID 1975463 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH2:36][NH:37][C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])[C:10](=O)[CH2:11][C@H:12]1[N:15]([C:16](=O)[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[C:14](=[O:24])[C@@H:13]1[C@H:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH3:26])=[O:6])[CH:2]=[CH2:3].P(OCC)(OCC)OCC.C1(C=CC(O)=CC=1)O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([C:10]1[CH2:11][C@H:12]2[N:15]([C:14](=[O:24])[C@@H:13]2[C@H:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:32])[CH3:33])([CH3:30])[CH3:29])[CH3:26])[C:16]=1[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH2:36][NH:37][C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 8857Ethyl AcetateHCID 31215Triethyl phosphiteHCID 67823630HCID 67823630, compound

Product 1

HCID 86747601HCID 86747601, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 0.48 g of allyl 2-[(3S,4R)-4-(4-allyloxycarbonylamino-3-(N-allyloxycarbonylaminomethyl)-2-oxobutyl]-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-oxoazetidin-1-yl]-2-oxoacetate and 0.39 ml of triethyl phosphite in 2.4 ml of toluene was stirred at 90° C. for 10 hours. After ylid was identified by thin layer chromatography the temperature was raised to 130° C. and 42 mg of hydroquinone was added. After stirring for 4 hours at 130° C., the reaction mixture was cooled to room temperature and then ethyl acetate was added. The organic layer was washed in turn with 5% aqueous potassium carbonate and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel to give 0.28 g of allyl (5R,6S)-3-[2-allyloxycarbonylamino-1-(N-allyloxycarbonylaminomethyl)ethyl]-6-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed in turn with 5% aqueous potassium carbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-75b98b83c37b49939ae410c4e984315f
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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