Acetic Acid → HCID 70507526, compound

HRID 2296563Notes

Reaction equation

[CH3:1][O:2][C:3]1([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22](=[O:23])[N:5]2[C:6]([C:11]([O:13][CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:12])=[C:7]([CH3:10])[C:8](=[O:9])[C@H:4]12.C(O)(=O)C>O1CCCC1.C1(C)C=CC=CC=1.[Zn]>[CH3:1][O:2][C:3]1([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22](=[O:23])[N:5]2[CH:6]([C:11]([O:13][CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:12])[CH:7]([CH3:10])[C:8](=[O:9])[C@H:4]12

Participants

Conditions

Temperature: 0 °C

Procedure

The freshly prepared pivaloyloxymethyl 6-methoxy-2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapen-2-em-3-carboxylate of Method B, Example 25, was dissolved in the minimum necessary tetrahydrofuran and added to a slurry of specially activated zinc powder (Example 2; 500 mg.) in a mixture of 1 ml. acetic acid and 0.5 ml. of tetrahydrofuran maintained at 0° C. After stirring for 1 hour at 0° C., the reaction mixture was diluted with toluene, evaporated to dryness in vacuo and chased several times with toluene. The residue was redissolved in methylene chloride, zinc removed by filtration, and the filtrate reconcentrated to dryness in vacuo. The residue was taken up in ether, insoluble impurities removed by filtration and the filtrate again evaporated to dryness in vacuo to yield pivaloyloxymethyl 6-methoxy-2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [20 mg.; Rf 0.70 (4:1 chloroform:ethyl acetate)].

Workup

customevaporated to dryness in vacuo
dissolutionThe residue was redissolved in methylene chloride
customzinc removed by filtration
custominsoluble impurities removed by filtration
customthe filtrate again evaporated to dryness in vacuo

Sources & evidence

ORD record: ord-885cd6a9a97f45f49ce50bc4c0c89e52
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04429128

Reaction notes

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