Acetic Acid → HCID 13065657, compound

HRID 2296548Notes

Reaction equation

HRID 2296548 reaction equation
[CH3:1][C:2]1[C:3](=[O:21])[C@@H:4]2[CH2:19][C:18](=[O:20])[N:5]2[C:6]=1[C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:8].O1CCCC1.C(O)(=O)C>[Ni].C1(C)C=CC=CC=1.C(Cl)Cl.[Zn]>[CH3:1][CH:2]1[CH:6]([C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:15])([CH3:16])[CH3:14])=[O:8])[N:5]2[C:18](=[O:20])[CH2:19][C@H:4]2[C:3]1=[O:21]

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 13065655HCID 13065655, compound

Product 1

HCID 13065657HCID 13065657, compound

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 23994ZincCatalystHCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Pivaloyloxymethyl 2-methyl-1-oxocarbapen-2-em-3-carboxylate, freshly prepared from 50 mg. of pivaloyloxymethyl 1-beta-oxo-2-diazo-3-methylceph-3-em-4-carboxylate by the method of Example 1 (employing the alternative Raney nickel step), was taken up in approximately 0.25 ml. of tetrahydrofuran and added to a slurry of 500 mg. of zinc powder, specially activated by the method of Rieke and Uhm [Synthesis, 452 (1975)], in 15 ml. of acetic acid-30% tetrahydrofuran at 0° C. After stirring for 1 hour at this temperature, the reaction mixture was diluted with toluene, stripped in vacuo and the residue chased several times with toluene. The vacuum pumped residue was taken up in excess methylene chloride, the zinc removed by filtration, and the filtrate reevaporated in vacuo to yield essentially homogeneous pivaloyloxymethyl 2-methyl-1-oxocarbapenam-3-carboxylate (tlc: Rf 0.45 with 18:1 chloroform:ethyl acetate as eluant; ir 1780, 1760 cm-1).

Workup

  1. customat 0° C
  2. customthe zinc removed by filtration
  3. customthe filtrate reevaporated in vacuo

Sources & evidence

ORD record
ord-9ac472b75bf0406e999fc2930446d501
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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