Acetic Acid → HCID 70507356, compound

HRID 1702716Notes

Reaction equation

HRID 1702716 reaction equation
[CH3:1][C:2]1[C:3](=[O:32])[C@@H:4]2[CH:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18](=[O:31])[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.[Zn]>[CH3:1][CH:2]1[CH:6]([C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:14])([CH3:15])[CH3:16])=[O:8])[N:5]2[C:18](=[O:31])[CH:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:4]2[C:3]1=[O:32]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 131712815HCID 131712815, compound

Product 1

HCID 70507356HCID 70507356, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

Freshly prepared pivaloyloxymethyl 2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapen-2-em-3-carboxylate (prepared from 200 mg. of pivaloyloxymethyl 2-diazo-3-methyl-1-beta-oxo-7-(2-phenoxyacetamido)ceph-3-em-4-carboxylate (incorporating a 2 g. Raney nickel treatment into the isolation step) was taken up in 1 ml. of tetrahydrofuran and added to a stirred slurry of 2 g. of specially activated zinc powder (Example 2), in 6 ml. of acetic acid containing 30% tetrahydrofuran maintained at 0°-5° C. After stirring for 1 hour at this temperature, the reaction mixture was diluted with toluene and evaporated to dryness in vacuo to yield pivaloyloxymethyl 2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [Rf 0.34 (9:1 chloroform:ethyl acetate; ir (CH2Cl2) 1790, 1750, 1680 cm-1 ].

Workup

  1. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-997c36bd840c4575b3c25274d99f85f7
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

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