Ethyl Acetate → HCID 58691124, compound

HRID 2376671Notes

Reaction equation

HRID 2376671 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=[C:8]2[C:12]([O:14]CC=C)=[O:13])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[Na+:55].C(OCC)(=O)C>C1COCC1.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.CCCCCC>[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=[C:8]2[C:12]([O-:14])=[O:13])[CH3:3].[Na+:55]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 58691142HCID 58691142, compound

Product 1

HCID 58691124HCID 58691124, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(3-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.37 g, 3.99 mmol) prepared by Reference Example 3, triphenylphosphine (52 mg), and tetrakis(triphenylphosphine)palladium(0) (0.23 g, 0.2 mmol) were dissolved in THF (20 ml), and thereto was added at 0° C. sodium 2-ethylhexanoate in ethyl acetate (0.5 M, 8.0 ml, 4.0 mmol), followed by stirring for 1 hour. Thereto was added hexane (30 ml) and the resulting white crystals were filtered under a nitrogen atmosphere, washed with hexane, dried at room temperature in vacuo to give a crude product. The product was dissolved in a small amount of ice-water, and purified with C18 reverse column chromatography (filler: Akosil 40C18 (Wako Pure Chemical Ind.); mobile phase; 0˜5%THF/ice-cooled ion-exchange water). The fractions containing the object compound were combined and THF therein was removed at room temperature in vacuo under stirring for 1 hour. The residue was lyophilized to give sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(3-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (297 mg, yield 23%).

Workup

  1. filtrationthe resulting white crystals were filtered under a nitrogen atmosphere
  2. washwashed with hexane
  3. customdried at room temperature in vacuo
  4. customto give a crude product
  5. custompurified with C18 reverse column chromatography (filler: Akosil 40C18 (Wako Pure Chemical Ind.); mobile phase; 0˜5%THF/ice-cooled ion-exchange water)
  6. additionThe fractions containing the object compound
  7. customTHF therein was removed at room temperature in vacuo
  8. stirringunder stirring for 1 hour

Sources & evidence

ORD record
ord-4e194dc75fb741118ed6fb3c96ebbfc7
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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