Acetic Acid → HCID 70507602, compound

HRID 2296567Notes

Reaction equation

HRID 2296567 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-97c62946ed6c4e518269db5c5e209448
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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