p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 178462281, compound

HRID 2289041Notes

Reaction equation

HRID 2289041 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:39](=[O:40])[N:6]2[C:7]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])=[C:8](OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].O[CH:42]([C@@H:68]1[CH2:72][C@H:71]([SH:73])[CH2:70][N:69]1[C:74]([O:76][CH2:77][C:78]1[CH:83]=[CH:82][C:81]([N+:84]([O-:86])=[O:85])=[CH:80][CH:79]=1)=[O:75])[CH2:43][C:44]([N:46]1[CH2:50][CH2:49][C@H:48]([NH:51][C:52](=[NH:67])[CH2:53][C:54]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][C:61]([N+:64]([O-:66])=[O:65])=[CH:60][CH:59]=2)=[O:55])[CH2:47]1)=[O:45]>>[OH:1][C@@H:2]([C@H:4]1[C:39](=[O:40])[N:6]2[C:7]([C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:27])=[C:8]([S:73][C@@H:71]3[CH2:70][N:69]([C:74]([O:76][CH2:77][C:78]4[CH:83]=[CH:82][C:81]([N+:84]([O-:86])=[O:85])=[CH:80][CH:79]=4)=[O:75])[C@@H:68]([CH2:42][CH2:43][C:44]([N:46]4[CH2:50][CH2:49][C@H:48]([NH:51][C:52](=[NH:67])[CH2:53][C:54]([O:56][CH2:57][C:58]5[CH:59]=[CH:60][C:61]([N+:64]([O-:66])=[O:65])=[CH:62][CH:63]=5)=[O:55])[CH2:47]4)=[O:45])[CH2:72]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

3

Reactant 2

HCID 15871605p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylateHCID 178511205HCID 178511205, compound

Product 1

HCID 178462281HCID 178462281, compoundYield 73.3%

Procedure

By using 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-(diphenylphosphoryloxy)-1-carbapen-2-em-3-carboxylate (563.2 mg) and (2S,4S)-2-[1-hydroxy-2-[(3S)-3-(4-nitrobenzyloxycarbonylacetimidoylamino)pyrrolidin-1-ylcarbonyl]ethyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (594.3 mg), reaction and purification were carried out in a similar manner to that described in Example 40-(1), whereby 4-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-2-[(2S,4S)-2-[(3S)-3-(4-nitrobenzyloxycarbonylacetimidoylamino)pyrrolidin-1-ylcarbonyl]ethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate (653.2 mg) was obtained as an amorphous substance.

Sources & evidence

ORD record
ord-74d3174de25e477dadd623cad659d976
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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