Acetic Acid → HCID 57082432, compound

HRID 1090554Notes

Reaction equation

HRID 1090554 reaction equation
C(OC([N:7]1[CH2:11][C@@H:10]([O:12][Si](C(C)(C)C)(C)C)[CH2:9][C@H:8]1[CH:20]=[C:21]([C:23]1[CH2:29][C@H:28]2[N:25]([C:26](=[O:40])[C@@H:27]2[C@H:30]([O:32][Si](C(C)(C)C)(C)C)[CH3:31])[C:24]=1[C:41]([O:43]CC=C)=[O:42])[CH3:22])=O)C=C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1.C(OCC)(=O)C>[OH:32][C@@H:30]([C@H:27]1[C:26](=[O:40])[N:25]2[C@@H:28]1[CH2:29][C:23]([C:21]([CH3:22])=[CH:20][C@@H:8]1[CH2:9][C@H:10]([OH:12])[CH2:11][NH:7]1)=[C:24]2[C:41]([OH:43])=[O:42])[CH3:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 56988112HCID 56988112, compound

Product 1

HCID 57082432HCID 57082432, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allyl (5R,6S)-3-[2-{(2S,4S)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)pyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.85 g) in tetrahydrofuran (20 ml) were added acetic acid (2.9 ml) and 1.0M solution of tetrabutylammonium fluoride in tetrahydrofuran (25.3 ml) in turn at ambient temperature. After stirring at ambient temperature for 9 hours, the solution was poured into a mixture of water (230 ml) and ethyl acetate (230 ml). The organic layer was separated, washed 5 times with water (100 ml), washed two times with brine (50 ml) dried over magnesium sulfate, and evaporated. To this residue were added tetrahydrofuran (10 ml), ethanol (3.5 ml) and triphenylphosphine (0.08 g). To this solution were added morpholine (0.28 ml) and tetrakis(triphenylphosphine)palladium(0) (0.11 g) successively at ambient temperature. Stirring at ambient temperature for 1 hour gave a precipitate, which was collected by filtration, washed with dichloromethane and dissolved in water (80 ml). The solution was washed with ethyl acetate (40 ml×3) and lyophilized to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[2-{(2S,4S)-4-hydroxypyrrolidin-2-yl}-1-methylethenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (155 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed 5 times with water (100 ml)
  3. washwashed two times with brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. additionTo this residue were added tetrahydrofuran (10 ml), ethanol (3.5 ml) and triphenylphosphine (0.08 g)
  7. additionTo this solution were added morpholine (0.28 ml) and tetrakis(triphenylphosphine)palladium(0) (0.11 g) successively at ambient temperature
  8. stirringStirring at ambient temperature for 1 hour
  9. customgave a precipitate, which
  10. filtrationwas collected by filtration
  11. washwashed with dichloromethane
  12. dissolutiondissolved in water (80 ml)
  13. washThe solution was washed with ethyl acetate (40 ml×3)

Sources & evidence

ORD record
ord-8c47b99fac0b4a6ea39f81e7c2f3a92f
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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