Phosphorus trichloride → HCID 178521147, compound

HRID 2071423Notes

Reaction equation

HRID 2071423 reaction equation
[C-:1]1([O:6][CH2:7][C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1.[Fe+2:16].P(Cl)(Cl)[Cl:18]>N1C=CC=CC=1.C1C=CC=CC=1>[C-:1]1([O:6][CH2:7][C:8]([Cl:18])=[O:10])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1.[Fe+2:16]

Participants

5

Reactant 2

HCID 24387Phosphorus trichlorideHCID 178525944HCID 178525944, compound

Product 1

HCID 178521147HCID 178521147, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 241BenzeneSolvent

Procedure

To ferrocenyloxyacetic acid (1.56 g, 0.006 m) and pyridine (4 drops) in benzene (100 cm3) was added dropwise phosphorous (III) chloride (5.4 cm3). The mixture was stirred for 3 hours at 60° to 70° C. After this time the benzene solution was decanted and the benzene removed under vacuum. The residue was taken up in benzene and the benzene again removed under vacuum. This procedure was repeated. Recrystallization from light petroleum (40° to 60°) gave 1.40 g (83.8%) of ferrocenyloxyacetyl chloride. The chloride (1.40g, 0.005 m) was taken up in dichloromethane (5cm3) and added dropwise to a mixture of 6-aminopenicillanic acid (1.08 g, 0.005 m) and triethylamine (1.01 g, 0.01 m) in dichloromethane (25 cm3) at 0° C. The mixture was stirred for 15 minutes at 0° C. and for 1 hour at 15° C. The solution was then filtered and the solvent removed under vacuum. The residue was taken up in a mixture of water (100 cm3) and ethyl acetate (25 cm3) and the aqueous layer adjusted to pH 2.5 with 2M HCl. The layers were separated and the ethyl acetate layer washed with water, dried, filtered and a 40% solution of SEH in 4-methylpentan-2-one (2 cm3) added. Worked up as previously the yield was 1.53 (67%) of the sodium salt of 6-(2-ferrocenyloxyacetamido) penicillanic acid. I.r. spectrum showed strong β-lactam absorption at 1770 cm-1.

Workup

  1. customAfter this time the benzene solution was decanted
  2. customthe benzene removed under vacuum
  3. customthe benzene again removed under vacuum
  4. customRecrystallization from light petroleum (40° to 60°)

Sources & evidence

ORD record
ord-f3862ab6c2c14fd5ad042077362fc6ec
Source dataset
uspto-grants-1977_09
Patent number
US04046903

Reaction notes

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