Acetic Acid → HCID 70590879, compound

HRID 261263Notes

Reaction equation

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

Participants

Conditions

Temperature: -15 °C

Procedure

2,2,2-Trichloroethyl 2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-2-methyl-6-[2-(1H-tetrazol-1-yl) acetamido]-penam-3-carboxylate (0.6 g) was dissolved in dimethylformamide (5 ml). To this solution were added acetic acid (0.9 ml) and zinc powder (0.8 g) under cooling at -15° C. and the mixture was stirred for 1.5 hours at the same temperature. After the reaction, zinc powder was filtered off and the filtrate was poured into 5% hydrochloric acid (20 ml) and then extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue was crystallized from ether to give 2-(1-methyl-1H-tetrazol-5-yl)thiomethyl-2-methyl-6-[2-(1H-tetrazol-1-yl) acetamido]penam-3-carboxylic acid (0.25 g), mp. 152° to 154° C.

Workup

filtrationwas filtered off
additionthe filtrate was poured into 5% hydrochloric acid (20 ml)
extractionextracted with ethyl acetate
washThe extract was washed with water
customdried
distillationthe solvent was distilled off
customThe residue was crystallized from ether

Sources & evidence

ORD record: ord-7ce34417c9324cba982fe8f616db5eb9
Source dataset: uspto-grants-1979_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04164497

Reaction notes

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