p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 178462044, compound

HRID 2289034Notes

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].[N+:41]([C:44]1[CH:101]=[CH:100][C:47]([CH2:48][O:49][C:50]([N:52]=[C:53]([NH:86][C:87]([O:89][CH2:90][C:91]2[CH:96]=[CH:95][C:94]([N+:97]([O-:99])=[O:98])=[CH:93][CH:92]=2)=[O:88])[NH:54][C@@H:55]([CH3:85])[C:56]([NH:58][C@H:59]2[CH2:63][CH2:62][N:61]([C:64]([C@@H:66]3[CH2:70][C@H:69]([SH:71])[CH2:68][N:67]3[C:72]([O:74][CH2:75][C:76]3[CH:81]=[CH:80][C:79]([N+:82]([O-:84])=[O:83])=[CH:78][CH:77]=3)=[O:73])=[O:65])[CH2:60]2)=[O:57])=[O:51])=[CH:46][CH:45]=1)([O-:43])=[O:42]>>[N+:41]([C:44]1[CH:45]=[CH:46][C:47]([CH2:48][O:49][C:50]([N:52]=[C:53]([NH:86][C:87]([O:89][CH2:90][C:91]2[CH:96]=[CH:95][C:94]([N+:97]([O-:99])=[O:98])=[CH:93][CH:92]=2)=[O:88])[NH:54][C@@H:55]([CH3:85])[C:56]([NH:58][C@H:59]2[CH2:63][CH2:62][N:61]([C:64]([C@@H:66]3[CH2:70][C@H:69]([S:71][C:8]4[C@H:9]([CH3:10])[C@@H:5]5[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:39](=[O:40])[N:6]5[C:7]=4[C:26]([O:28][CH2:29][C:30]4[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=4)=[O:27])[CH2:68][N:67]3[C:72]([O:74][CH2:75][C:76]3[CH:81]=[CH:80][C:79]([N+:82]([O-:84])=[O:83])=[CH:78][CH:77]=3)=[O:73])=[O:65])[CH2:60]2)=[O:57])=[O:51])=[CH:100][CH:101]=1)([O-:43])=[O:42]

Participants

Reactant 2

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

HCID 178462045HCID 178462045, compound

Product 1

HCID 178462044HCID 178462044, compoundYield 81.8%

Procedure

By using 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-diphenylphosphoryloxy-1-carbapen-2-em-3-carboxylate (1.21 g) and (2S,4S)-2-[(3S)-3-[(2S)-2-[2,3-di(4-nitrobenzyloxycarbonyl)guanidino]-2-methylacetylamino]-pyrrolidin-1-ylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.68 g), 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)-2-[(3S)-3-[(2S)-2-[2,3-di(4-nitrobenzyloxycarbonyl)guanidino]-2-methylacetylamino]pyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (1.92 g) was obtained as an amorphous substance.

Sources & evidence

ORD record: ord-f6001f109fd34c3ebefcdd7c0bbce3da
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090802

Reaction notes

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