Acetic Acid → HCID 57062899, compound

HRID 1650319Notes

Reaction equation

HRID 1650319 reaction equation
C(OC([N:7]1[CH2:11][C@@H:10]([N:12](C(OCC=C)=O)[CH3:13])[CH2:9][C@H:8]1[CH:20]=[C:21]([C:23]1[CH2:29][C@H:28]2[N:25]([C:26](=[O:33])[C@@H:27]2[C@H:30]([OH:32])[CH3:31])[C:24]=1[C:34]([O:36]CC=C)=[O:35])[CH3:22])=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C>O1CCCC1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:32][C@@H:30]([C@H:27]1[C:26](=[O:33])[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]([NH:12][CH3:13])[CH2:11][NH:7]1)=[C:24]2[C:34]([OH:36])=[O:35])[CH3:31]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 56977303HCID 56977303, compound

Product 1

HCID 57062899HCID 57062899, compoundYield 44.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl (5R,6S)-3-[2-{(2S,4S)-1-allyloxycarbonyl-4-(N-allyloxycarbonyl-N-methylamino)-pyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1hydroxyethyl]-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylate (0.495 g) in a mixture of tetrahydrofuran (5 ml) and ethanol (2.5 ml) were added successively triphenylphosphine (96 mg), 5.5-dimethyl-1,3-cyclohxanedione (dimedone)(0.38 g), acetic acid (54.7 μl), and tetrakis(triphenylphosphine)palladium(0) (85 mg). Stirring at ambient temperature for 1 hour gave a precipitate, which was coolected by filtration, washed with ethyl acetate and dissolved in water (70 ml). The solution was washed with ethyl acetate (30 ml×3) and concentrated in vacuo. The residue was chromatographed on nonionic adsorption resin "Diaion HP-20" (Trademark, made by Mitsubishi Chemical Industries)(70 ml) eluting with aqueous isopropyl alcohol (3%-20%). The fractions containing the desired compound were collected and lyophilized to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[2-{(2S,4S)-4-(methylamino)-pyrrolidin-2-yl}-1-methylethenyl]-7-oxo-1-azabicyclo-[3.2.0]hept-2-ene-2-carboxylic acid (135 mg).

Workup

  1. customgave a precipitate, which
  2. filtrationwas coolected by filtration
  3. washwashed with ethyl acetate
  4. dissolutiondissolved in water (70 ml)
  5. washThe solution was washed with ethyl acetate (30 ml×3)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on nonionic adsorption resin "Diaion
  8. wash" (Trademark, made by Mitsubishi Chemical Industries)(70 ml) eluting with aqueous isopropyl alcohol (3%-20%)
  9. additionThe fractions containing the desired compound
  10. customwere collected

Sources & evidence

ORD record
ord-5355890f203041cb86e2158a38844560
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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