p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 57264755, compound

HRID 2289029Notes

Reaction equation

HRID 2289029 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]([CH2:60][C:61]([N:63]2[CH2:67][CH2:66][C@H:65]([NH:68][C:69]([O:71][CH2:72][C:73]3[CH:78]=[CH:77][C:76]([N+:79]([O-:81])=[O:80])=[CH:75][CH:74]=3)=[O:70])[CH2:64]2)=[O:62])[CH2:43]1>C(#N)C.C(N(C(C)C)CC)(C)C>[N+:57]([C:54]1[CH:55]=[CH:56][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:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=3)=[O:22])[CH2:43][C@H:44]2[CH2:60][C:61]([N:63]2[CH2:67][CH2:66][C@H:65]([NH:68][C:69]([O:71][CH2:72][C:73]3[CH:74]=[CH:75][C:76]([N+:79]([O-:81])=[O:80])=[CH:77][CH:78]=3)=[O:70])[CH2:64]2)=[O:62])=[O:48])=[CH:52][CH:53]=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 57153243HCID 57153243, compound

Product 1

HCID 57264755HCID 57264755, compoundYield 94.6%

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 (478 mg) in anhydrous acetonitrile (5.5 ml), a solution of (2R,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[(3S)-3-(4-nitrobenzyloxycarbonylamino)pyrrolidin-1-ylcarbonylmethyl]pyrrolidine (450 mg) in anhydrous acetonitrile (5.5 ml) and diisopropylethylamine (0.140 ml) were added under ice cooling. The resulting mixture was allowed to stand for one day at the same temperature. The reaction mixture was concentrated by evaporation under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with water and saline, dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was subjected to chromatography on a silica gel column. From the fraction eluted with ethyl acetate-methanol (20:1), 4-nitrobenzyl (1R,5R,6S)-2-[(2R,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[(3S)-3-(4-nitrobenzyloxycarbonylamino)pyrrolidin-1-ylcarbonylmethyl]pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (675 mg) 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 with water and saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. washFrom the fraction eluted with ethyl acetate-methanol (20:1)

Sources & evidence

ORD record
ord-f9dd50c310e446139e67aa51bd738c9a
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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