(4-Nitrophenyl)methyl (5R,6S)-6-((1R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo(3.2.0)heptane-2-carboxylate → (5R, 6S)-2-[(2S, 4S)-1-Ethyl-1-methyl-2-(N,N-dimethylcarbamoyl)pyrrolidinium-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

HRID 5060Notes

Reaction equation

HRID 5060 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[CH:7]([C:11]([O:13]CC3C=CC([N+]([O-])=O)=CC=3)=[O:12])[C:8](=O)[CH2:9][C@H:5]12)[CH3:3].[CH3:26][N:27]([CH3:39])[C:28]([C@@H:30]1[CH2:34][C@H:33]([SH:35])[CH2:32][N+:31]1([CH2:37][CH3:38])[CH3:36])=[O:29]>>[CH2:37]([N+:31]1([CH3:36])[CH2:32][C@@H:33]([S:35][C:8]2[CH2:9][C@@H:5]3[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:24](=[O:25])[N:6]3[C:7]=2[C:11]([O-:13])=[O:12])[CH2:34][C@H:30]1[C:28](=[O:29])[N:27]([CH3:26])[CH3:39])[CH3:38]

Participants

3

Reactant 2

HCID 11198839(4-Nitrophenyl)methyl (5R,6S)-6-((1R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo(3.2.0)heptane-2-carboxylateHCID 131718110(2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-1-methyl-4-mercaptopyrrolidinium

Product 1

HCID 131718109(5R, 6S)-2-[(2S, 4S)-1-Ethyl-1-methyl-2-(N,N-dimethylcarbamoyl)pyrrolidinium-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylateYield 10.1%

Procedure

Following a procedure similar to that described in Example 6, but using 459 mg of 4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate and 580 mg of the crude (2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-1-methyl-4-mercaptopyrrolidinium salt [prepared as described in Example 9-(2)], 55 mg of the title compound were obtained.

Sources & evidence

ORD record
ord-c134e3f71f3f457ca6e219a28a76ce5e
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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