HCID 131712819, compound → HCID 70507886, compound

HRID 2296570Notes

Reaction equation

HRID 2296570 reaction equation
[CH3:1][C:2]1[C:3](=[O:37])[C@@H:4]2[CH:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23](=[O:36])[N:5]2[C:6]=1[C:7]([O:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]>[Zn].C(O)(=O)C>[CH3:1][CH:2]1[CH:6]([C:7]([O:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[N:5]2[C:23](=[O:36])[CH:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:4]2[C:3]1=[O:37]

Participants

4

Reactant 1

HCID 131712819HCID 131712819, compound

Product 1

HCID 70507886HCID 70507886, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

The pivaloyloxymethyl 2-methyl-6-(5-methyl-3-phenylisoxazole-4-carboxamido)-1-oxocarbapen-2-em-3-carboxylate of Example 35 was reduced with zinc (2.22 g.) in 5.3 ml. of acetic acid-30% tetrahydrofuran, by methods detailed in Example 2, and isolated according to methods detailed in Examples 2 and 32, affording pivaloyloxymethyl 2-methyl-6-(5-methyl-3-phenylisoxazole-4-carboxamido)-1-oxocarbapenam-3-carboxylate [100 mg., 50% over-all; ir (CH2Cl2) 1790, 1750, 1670 cm-1 ].

Workup

  1. customisolated

Sources & evidence

ORD record
ord-e87ba907c6854623916544396fa0be91
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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