Water → HCID 15117355, compound

HRID 1029683Notes

Reaction equation

HRID 1029683 reaction equation
C(OC([N:7]1[CH2:12][CH:11]=[C:10]([C:13]2[CH2:19][C@H:18]3[N:15]([C:16](=[O:23])[C@@H:17]3[C@H:20]([OH:22])[CH3:21])[C:14]=2[C:24]([O:26]CC=C)=[O:25])[CH2:9][CH2:8]1)=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1(C)CC(=O)CC(=O)C1.O>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[OH:22][C@@H:20]([C@H:17]1[C:16](=[O:23])[N:15]2[C@@H:18]1[CH2:19][C:13]([C:10]1[CH2:11][CH2:12][NH:7][CH2:8][CH:9]=1)=[C:14]2[C:24]([OH:26])=[O:25])[CH3:21]

Participants

8

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 31358DimedoneHCID 15117353HCID 15117353, compound

Product 1

HCID 15117355HCID 15117355, compoundYield 35.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allyl (5R,6S)-3-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.280 g) in tetrahydrofuran (9 ml) were added successively triphenylphosphine (0.094 g), 5,5-dimethyl-1,3-cyclohexanedione (dimedone) (0.201 g) and tetrakis(triphenylphosphine) palladium(0) (41.5 mg). After stirring at ambient temperature for 1 hour, the mixture was poured into a mixture of cold water (50 ml) and ethyl acetate (30 ml). The separated aqueous layer was washed with ethyl acetate (30 ml×2) and concentrated in vacuo to remove the organic solvent. The residue was chromatographed on acid aluminum oxide (3 ml) eluting with water. The fractions containing the desired compound were collected and chromatographed on nonionic adsorption resin, "Diaion HP-20" (Trademark, made by Mitsubishi Chemical Industries) (20 ml) eluting with water. The fractions containing the desired compound were collected and lyophilized to give (5R,6S)-6-[ (1R)-1-hydroxyethyl]-7-oxo-3-(1,2,3,6-tetrahydropyridin-4-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (68 mg).

Workup

  1. washThe separated aqueous layer was washed with ethyl acetate (30 ml×2)
  2. concentrationconcentrated in vacuo
  3. customto remove the organic solvent
  4. customThe residue was chromatographed on acid aluminum oxide (3 ml)
  5. washeluting with water
  6. additionThe fractions containing the desired compound
  7. customwere collected
  8. customchromatographed on nonionic adsorption resin, "Diaion
  9. wash" (Trademark, made by Mitsubishi Chemical Industries) (20 ml) eluting with water
  10. additionThe fractions containing the desired compound
  11. customwere collected

Sources & evidence

ORD record
ord-3d338b55ec3b48ee902d3eeeb95a6e8e
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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