Acetic Acid → HCID 70507602, compound

HRID 1702726Notes

Reaction equation

HRID 1702726 reaction equation
[CH3:1][C:2]1[C:3](=[O:47])[C@@H:4]2[CH:22]([NH:23][C:24](=[O:45])[CH:25]([NH:32][C:33]([N:35]3[CH2:40][CH2:39][N:38]([CH2:41][CH3:42])[C:37](=[O:43])[C:36]3=[O:44])=[O:34])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:21](=[O:46])[N:5]2[C:6]=1[C:7]([O:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[O:8].O1CCCC1.C(O)(=O)C>CCOCC.[Zn]>[CH3:1][CH:2]1[CH:6]([C:7]([O:9][CH2:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[O:8])[N:5]2[C:21](=[O:46])[CH:22]([NH:23][C:24](=[O:45])[CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:32][C:33]([N:35]3[CH2:40][CH2:39][N:38]([CH2:41][CH3:42])[C:37](=[O:43])[C:36]3=[O:44])=[O:34])[C@H:4]2[C:3]1=[O:47]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 131712818HCID 131712818, compound

Product 1

HCID 70507602HCID 70507602, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Procedure

The 2-naphthylmethyl 2-methyl-1-oxo-6-[2-phenyl-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapen-2-em-3-carboxylate of Example 31 was taken up in a minimum of tetrahydrofuran, and added to a slurry of activated zinc (2.37 g.) in 5 ml. of acetic acid-30% tetrahydrofuran at 0° C. After 1 hour at 0° C., product was isolated according to procedures detailed in Example 2. The resulting product was taken up in ether, insolubles removed by filtration, and the filtrate evaporated to dryness in vacuo to yield 2-naphthylmethyl 2-methyl-1-oxo-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate [36 mg., 16%; Rf 0.48 (ethyl acetate)].

Workup

  1. customat 0° C
  2. customproduct was isolated
  3. custominsolubles removed by filtration
  4. customthe filtrate evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-6357a971bcff446995401004fbb513a6
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

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