Triphenylphosphine → HCID 22807221, compound

HRID 614555Notes

Reaction equation

HRID 614555 reaction equation
[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6](C(O)=O)/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC([N+](=NC(OCC)=O)[O-])=O)C>O1CCCC1.CCOCC.CCCCC>[O:5]=[C:4]1[N:3]2[C@H:2]([O:11][C:7]([CH:8]=[CH2:9])=[CH:6]2)[CH2:1]1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 5280980Clavulanic AcidHCID 131711458HCID 131711458, compound

Product 1

HCID 22807221HCID 22807221, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Clavulanic acid (1.5 mmole) in dry tetrahydrofuran (5 ml) under a dry nitrogen atmosphere was treated with triphenylphosphine (1.5 mmole) and then, dropwise, diethylazoxicarboxylate (1.5 mmole) in dry tetrahydrofuran (2 ml). After addition was complete (2 minutes), the mixture was stirred for 30 minutes at room temperature and was then ice-cooled and diluted with a mixture of ether and n-pentane (1:2, 20 ml). The mixture was filtered and the filtrate was diluted with dry benzene (10 ml) and then concentrated to about 5 ml under reduced pressure to yield a solution of the title compound (1 mmole).

Workup

  1. additionAfter addition
  2. custom(2 minutes)
  3. temperatureice-cooled
  4. filtrationThe mixture was filtered
  5. additionthe filtrate was diluted with dry benzene (10 ml)
  6. concentrationconcentrated to about 5 ml under reduced pressure

Sources & evidence

ORD record
ord-34b7a54a358440d7a798a5985e355b41
Source dataset
uspto-grants-1979_03
Patent number
US04145430

Reaction notes

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