p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 131721892, compound

HRID 2289030Notes

Reaction equation

HRID 2289030 reaction equation
C1(P(O[C:16]2[C@H:17]([CH3:40])[C@@H:18]3[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]3[C:20]=2[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)=[O:22])(C2C=CC=CC=2)=O)C=CC=CC=1.[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](/[CH:60]=[CH:61]/[C:62]([N:64]2[CH2:68][CH2:67][C@H:66]([NH:69][C:70]([O:72][CH2:73][C:74]3[CH:79]=[CH:78][C:77]([N+:80]([O-:82])=[O:81])=[CH:76][CH:75]=3)=[O:71])[CH2:65]2)=[O:63])[CH2:43]1>C(#N)C.C(N(C(C)C)CC)(C)C>[N+:57]([C:54]1[CH:53]=[CH:52][C:51]([CH2:50][O:49][C:47]([N:45]2[CH2:46][C@@H:42]([S:41][C:16]3[C@H:17]([CH3:40])[C@@H:18]4[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]4[C:20]=3[C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[CH2:43][C@@H:44]2/[CH:60]=[CH:61]/[C:62]([N:64]2[CH2:68][CH2:67][C@H:66]([NH:69][C:70]([O:72][CH2:73][C:74]3[CH:75]=[CH:76][C:77]([N+:80]([O-:82])=[O:81])=[CH:78][CH:79]=3)=[O:71])[CH2:65]2)=[O:63])=[O:48])=[CH:56][CH:55]=1)([O-:59])=[O:58]

Participants

5

Reactant 2

HCID 15871605p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylateHCID 88248630HCID 88248630, compound

Product 1

HCID 131721892HCID 131721892, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 4-nitrobenzyl (1R,5R,6S)-2-(diphenylphosphoryloxy)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (1.01 g) in anhydrous acetonitrile (10 ml), a solution of (2R,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[(3S)-3-(4-nitrobenzyloxycarbonylamino)pyrrolidin-1-ylcarbonyl-(E)-ethenyl]-pyrrolidine (972 mg) in anhydrous acetonitrile (10 ml) and diisopropylethylamine (0.296 ml) were added under ice cooling. The resulting mixture was allowed to stand at the same temperature for one day. The reaction mixture was concentrated by evaporation under reduced pressure and the residue was extracted with ethyl acetate. The extract was washed successively with water and saline and then dried over anhydrous sodium sulfate. The solvent was distilled off. The residue was subjected to chromatography on a silica gel column and eluted with methylene chloride-acetone of ratio from (6:1) to (1:1). Desired fractions were combined, followed by distilling off, whereby 4-nitrobenzyl (1R,5S,6S)-2-[(2R,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[(3S)-3-(4-nitrobenzyloxycarbonylamino)pyrrolidin-1-ylcarbonyl-(E)-ethenyl]pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (1.079 g) was obtained as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. washeluted with methylene chloride-acetone of ratio from (6:1) to (1:1)
  7. distillationby distilling off

Sources & evidence

ORD record
ord-8dc9163c95334a25beedacaec7acd57c
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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