Diisopropylethylamine → HCID 131720446, compound

HRID 727715Notes

Reaction equation

HRID 727715 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.C(N(C(C)C)CC)(C)C.[SH:50][C@@H:51]1[CH2:55][N:54]([C:56]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][C:63]([N+:66]([O-:68])=[O:67])=[CH:62][CH:61]=2)=[O:57])[C@H:53]([C:69]([N:71]2[CH2:74][CH:73]([N:75]3[CH:79]=[N:78][CH:77]=[N:76]3)[CH2:72]2)=[O:70])[CH2:52]1>C(#N)C>[OH:38][C@@H:36]([C@H:35]1[C:34](=[O:39])[N:19]2[C:20]([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])=[C:16]([S:50][C@@H:51]3[CH2:55][N:54]([C:56]([O:58][CH2:59][C:60]4[CH:65]=[CH:64][C:63]([N+:66]([O-:68])=[O:67])=[CH:62][CH:61]=4)=[O:57])[C@H:53]([C:69]([N:71]4[CH2:72][CH:73]([N:75]5[CH:79]=[N:78][CH:77]=[N:76]5)[CH2:74]4)=[O:70])[CH2:52]3)[C@H:17]([CH3:40])[C@H:18]12)[CH3:37]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15871605p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylateHCID 86752014HCID 86752014, compound

Product 1

HCID 131720446HCID 131720446, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

886 mg of 4-nitrobenzyl (1R,5R,6S)-2-(diphenylphosphoryloxy)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (prepared as described in Preparation 123) was dissolved in 10 ml of dry acetonitrile, and 0.26 ml of diisopropylethylamine and 873 mg of (2S,4S)-4-mercapto-2-[3-(1-1,2,4-triazolyl)-1-azetidinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (prepared as described in Preparation 120) dissolved in 5 ml of acetonitrile were added dropwise at the same time to the resulting solution, whilst ice-cooling. The mixture was then stirred at the same temperature for 3 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was diluted with ethyl acetate. The resulting mixture was washed with water, with an aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride. The aqueous layer was dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue was purified by silica gel column chromatography, using a gradient solution method, with mixtures of ethyl acetate and methanol ranging from 6:1 to 4:1 by volume as the eluent, to obtain 661 mg of the title compound, as a powder.

Workup

  1. additionwere added dropwise at the same time to the resulting solution, whilst ice-
  2. temperaturecooling
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washThe resulting mixture was washed with water, with an aqueous solution of sodium hydrogencarbonate, with water and with a saturated aqueous solution of sodium chloride
  6. dry with materialThe aqueous layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d2e1e30c18e14d1db3be140d71d76e87
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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