Triphenylphosphine → HCID 58691129, compound

HRID 2376674Notes

Reaction equation

HRID 2376674 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:16][C@H:15]3[N:12]([C:13](=[O:20])[C@@H:14]3[C@H:17]([OH:19])[CH3:18])[C:11]=2[C:21]([O:23]CC=C)=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[Na+:56]>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>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:16][C@H:15]3[N:12]([C:13](=[O:20])[C@@H:14]3[C@H:17]([OH:19])[CH3:18])[C:11]=2[C:21]([O-:23])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Na+:56]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 58691131HCID 58691131, compound

Product 1

HCID 58691129HCID 58691129, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Allyl (5R,6S)-3-(3-fluoro-4-methoxyphenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.807 g), tetrakis(triphenylphosphine)palladium(0) (50 mg) and triphenylphosphine (10 mg) were dissolved in THF (12 mL), and thereto was added at room temperature sodium 2-ethylhexanoate (0.5M ethyl acetate solution, 4.46 mL). The solvent was removed in vacuo, and to the residue was added dichloromethane (10 mL). The mixture was extracted with ion-exchange water (10 mL×3 times) and the aqueous layers were combined and stirred for 1 hour in vacuo. The dichloromethane was removed by distillation and the aqueous layer was purified with C18 reverse column chromatography (Wakosil 40C18, 38φ×60 mm, mobile phase; 0˜5% THF ice-cooled ion-exchange water). The fractions containing the object compound were combined and THF therein was removed in vacuo under stirring for 1 hour. The residue was lyophilized to give sodium (5R,6S)-3-(3-fluoro-4-methoxyphenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (450 mg, yield 59%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionto the residue was added dichloromethane (10 mL)
  3. extractionThe mixture was extracted with ion-exchange water (10 mL×3 times)
  4. customThe dichloromethane was removed by distillation
  5. customthe aqueous layer was purified with C18 reverse column chromatography (Wakosil 40C18, 38φ×60 mm, mobile phase; 0˜5% THF ice-cooled ion-exchange water)
  6. additionThe fractions containing the object compound
  7. customTHF therein was removed in vacuo
  8. stirringunder stirring for 1 hour

Sources & evidence

ORD record
ord-b728f040e8ef472086c2a8a0afe7a709
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

Loading…