p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 178462287, compound

HRID 2289028Notes

Reaction equation

HRID 2289028 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].[SH:41][C@@H:42]1[CH2:46][N:45]([C:47]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][C:54]([N+:57]([O-:59])=[O:58])=[CH:53][CH:52]=2)=[O:48])[C@H:44]([C:60]([N:62]2[CH2:66][CH2:65][C@H:64]([N:67]([C:75]([O:77][CH2:78][C:79]3[CH:84]=[CH:83][C:82]([N+:85]([O-:87])=[O:86])=[CH:81][CH:80]=3)=[O:76])[C:68](=[O:74])[CH2:69][NH:70][C:71]([NH2:73])=[NH:72])[CH2:63]2)=[O:61])[CH2:43]1>>[N+:57]([C:54]1[CH:55]=[CH:56][C:51]([CH2:50][O:49][C:47]([N:45]2[CH2:46][C@@H:42]([S:41][C:8]3[C@H:9]([CH3:10])[C@@H:5]4[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:39](=[O:40])[N:6]4[C:7]=3[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])[CH2:43][C@H:44]2[C:60]([N:62]2[CH2:66][CH2:65][C@H:64]([N:67]([C:75]([O:77][CH2:78][C:79]3[CH:84]=[CH:83][C:82]([N+:85]([O-:87])=[O:86])=[CH:81][CH:80]=3)=[O:76])[C:68](=[O:74])[CH2:69][NH:70][C:71]([NH2:73])=[NH:72])[CH2:63]2)=[O:61])=[O:48])=[CH:52][CH:53]=1)([O-:59])=[O:58]

Participants

3

Reactant 2

HCID 15871605p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylateHCID 178513021HCID 178513021, compound

Product 1

HCID 178462287HCID 178462287, compoundYield 49.6%

Procedure

By using 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-(diphenylphosphoryloxy)-1-carbapen-2-em-3-carboxylate (697 mg) and (2S,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[(3S)-3-[(4-nitrobenzyloxycarbonyl)guanidinoacetylamino]pyrrolidin-1-ylcarbonyl]pyrrolidine (751 mg), reaction and purification were carried out in a similar manner to that described in Example 1-(1), whereby 4-nitrobenzyl (1R,5S,6S)-2-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[(3S)-3-[(4-nitrobenzyloxycarbonyl)guanidinoacetylamino]pyrrolidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (563 mg) was obtained as a powder.

Sources & evidence

ORD record
ord-dfd45f1d6ade4d14b88f7446bd403df5
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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