p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 131721895, compound

HRID 2289032Notes

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].[CH:41]1([CH2:47][C@H:48]([NH:81][C:82]([O:84][CH2:85][C:86]2[CH:91]=[CH:90][C:89]([N+:92]([O-:94])=[O:93])=[CH:88][CH:87]=2)=[O:83])[C@@H:49]([OH:80])[CH2:50][C:51]([NH:53][C@H:54]2[CH2:58][CH2:57][N:56]([C:59]([C@@H:61]3[CH2:65][C@H:64]([SH:66])[CH2:63][N:62]3[C:67]([O:69][CH2:70][C:71]3[CH:76]=[CH:75][C:74]([N+:77]([O-:79])=[O:78])=[CH:73][CH:72]=3)=[O:68])=[O:60])[CH2:55]2)=[O:52])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>>[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:66][C@@H:64]3[CH2:63][N:62]([C:67]([O:69][CH2:70][C:71]4[CH:72]=[CH:73][C:74]([N+:77]([O-:79])=[O:78])=[CH:75][CH:76]=4)=[O:68])[C@H:61]([C:59]([N:56]4[CH2:57][CH2:58][C@H:54]([NH:53][C:51](=[O:52])[CH2:50][C@H:49]([OH:80])[C@@H:48]([NH:81][C:82]([O:84][CH2:85][C:86]5[CH:91]=[CH:90][C:89]([N+:92]([O-:94])=[O:93])=[CH:88][CH:87]=5)=[O:83])[CH2:47][CH:41]5[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]5)[CH2:55]4)=[O:60])[CH2:65]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 57258141HCID 57258141, compound

Product 1

HCID 131721895HCID 131721895, compoundYield 72.6%

Procedure

By using 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-diphenylphosphoryloxy-1-carbapen-2-em-3-carboxylate (1.53 g) and (2S,4S)-2-[(3S)-3-[(3S,4S)-5-cyclohexyl-3-hydroxy-4-(4-nitrobenzyloxycarbonyl)aminopentanoylamino]pyrrolidin-1-ylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.00 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-[(3S,4S)-5-cyclohexyl-3-hydroxy-4-(4-nitrobenzyloxycarbonyl)aminopentanoylamino]pyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate (2.10 g) was obtained as an amorphous substance.

Sources & evidence

ORD record: ord-4865c96ac5be4fd3b751fb02e2ab4e1f
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090802

Reaction notes

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