HCID 57110108, compound → HCID 131721893, compound

HRID 2289031Notes

Reaction equation

HRID 2289031 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:38](=[O:39])[N:6]2[C:7]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)=[O:26])=[C:8](P(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[C@H:9]([CH3:10])[C@@H:5]12)[CH3:3].[OH:40][CH:41]([CH2:72][NH:73][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])[CH2:42][C:43]([NH:45][C@H:46]1[CH2:50][CH2:49][N:48]([C:51]([C@@H:53]2[CH2:57][C@H:56]([SH:58])[CH2:55][N:54]2[C:59]([O:61][CH2:62][C:63]2[CH:68]=[CH:67][C:66]([N+:69]([O-:71])=[O:70])=[CH:65][CH:64]=2)=[O:60])=[O:52])[CH2:47]1)=[O:44]>>[OH:1][C@@H:2]([C@H:4]1[C:38](=[O:39])[N:6]2[C:7]([C:25]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=3)=[O:26])=[C:8]([S:58][C@@H:56]3[CH2:55][N:54]([C:59]([O:61][CH2:62][C:63]4[CH:64]=[CH:65][C:66]([N+:69]([O-:71])=[O:70])=[CH:67][CH:68]=4)=[O:60])[C@H:53]([C:51]([N:48]4[CH2:49][CH2:50][C@H:46]([NH:45][C:43](=[O:44])[CH2:42][CH:41]([OH:40])[CH2:72][NH:73][C:74]([O:76][CH2:77][C:78]5[CH:79]=[CH:80][C:81]([N+:84]([O-:86])=[O:85])=[CH:82][CH:83]=5)=[O:75])[CH2:47]4)=[O:52])[CH2:57]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

3

Reactant 2

HCID 57110108HCID 57110108, compoundHCID 131721894HCID 131721894, compound

Product 1

HCID 131721893HCID 131721893, compoundYield 83.4%

Procedure

By using 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-diphenylphosphoryl-1-carbapen-2-em-3-carboxylate (1.78 g) and (2S,4S)-2-[(3S)-3-[3-hydroxy-4-(4-nitrobenzyloxycarbonyl)aminobutanoylamino]pyrrolidin-1-ylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.0 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-[3-hydroxy-4-(4-nitrobenzyloxycarbonyl)aminobutanoylamino]pyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate (2.52 g) was obtained as an amorphous substance.

Sources & evidence

ORD record
ord-9a415037b3be45e789da6a9b4be9cede
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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