p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 131721898, compound

HRID 2289035Notes

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].[CH3:41][N:42]([CH2:72][C:73]([NH:75][C@H:76]1[CH2:80][CH2:79][N:78]([C:81]([C@@H:83]2[CH2:87][C@H:86]([SH:88])[CH2:85][N:84]2[C:89]([O:91][CH2:92][C:93]2[CH:98]=[CH:97][C:96]([N+:99]([O-:101])=[O:100])=[CH:95][CH:94]=2)=[O:90])=[O:82])[CH2:77]1)=[O:74])[C:43]([NH:58][C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([N+:69]([O-:71])=[O:70])=[CH:65][CH:64]=1)=[O:60])=[N:44][C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][C:52]([N+:55]([O-:57])=[O:56])=[CH:51][CH:50]=1)=[O:46]>>[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:88][C@@H:86]3[CH2:85][N:84]([C:89]([O:91][CH2:92][C:93]4[CH:98]=[CH:97][C:96]([N+:99]([O-:101])=[O:100])=[CH:95][CH:94]=4)=[O:90])[C@H:83]([C:81]([N:78]4[CH2:79][CH2:80][C@H:76]([NH:75][C:73](=[O:74])[CH2:72][N:42]([CH3:41])[C:43]([NH:58][C:59]([O:61][CH2:62][C:63]5[CH:64]=[CH:65][C:66]([N+:69]([O-:71])=[O:70])=[CH:67][CH:68]=5)=[O:60])=[N:44][C:45]([O:47][CH2:48][C:49]5[CH:54]=[CH:53][C:52]([N+:55]([O-:57])=[O:56])=[CH:51][CH:50]=5)=[O:46])[CH2:77]4)=[O:82])[CH2:87]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

Reactant 2

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

HCID 57246304HCID 57246304, compound

Product 1

HCID 131721898HCID 131721898, compoundYield 53.5%

Procedure

By using 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-diphenylphosphoryloxy-1-carbapen-2-em-3-carboxylate (936 mg) and (2S,4S)-2-[(3S)-3-[2-[1-methyl-2,3-di(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.30 g), reaction and purification were carried out in a similar manner to that described in Example 1-(1), whereby 4-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-2-[(2S,4S)-2-[(3S)-3-[2-[1-methyl-2,3-di(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate (972 mg) was obtained as an amorphous substance.

Sources & evidence

ORD record: ord-582f6d52f99b4b72b2e948ca1f2e8857
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090802

Reaction notes

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