Acetic Acid → HCID 70506715, compound

HRID 2296565Notes

Reaction equation

[CH3:1][C:2]1[C:3](=[O:44])[C@@H:4]2[CH:19]([NH:20][C:21](=[O:42])[CH:22]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:23][C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[C:28](=[O:34])[C:27]3=[O:35])=[O:25])[C:18](=[O:43])[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].S1[C@@H]2CC(=O)N2C=CC1.O1CCCC1.C(O)(=O)C>[Zn].CCOCC>[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:43])[CH:19]([NH:20][C:21](=[O:42])[CH:22]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[NH:23][C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[C:28](=[O:34])[C:27]3=[O:35])=[O:25])[C@H:4]2[C:3]1=[O:44]

Participants

Conditions

Temperature: 0 °C

Procedure

Pivaloyloxymethyl 2-methyl-1-oxo-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapen-2-em-3-carboxylate [freshly prepared according to Example 28 from 127 mg. (0.19 mmole) of the ceph-3-em precursor] was taken up in a minimum of tetrahydrofuran and added to a slurry of activated zinc powder (1.27 g.) in a mixture of 26 ml. of acetic acid and 12 ml. of tetrahydrofuran at 0° C. Stirring at 0° C. was continued for 1 hour. Product was isolated according to procedures detailed in Example 2, followed by trituration with ether, yielding pivaloyloxymethyl 2-methyl-1-oxo-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate [30 mg.; Rf 0.91 (ethyl acetate)]. An additional 13 mg. of less pure product was obtained by evaporation of the ether triturate to dryness.

Workup

customat 0° C
customProduct was isolated

Sources & evidence

ORD record: ord-15dc37ad4d484c91a611effdf39c35f1
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04429128

Reaction notes

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