HCID 19971504, compound → HCID 86750489, compound

HRID 975726Notes

Reaction equation

HRID 975726 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH2:9][C@H:8]1[CH2:31][CH2:32][N:33]1[CH:37]=[CH:36][N:35]=[CH:34]1)=[O:6])[CH:2]=[CH2:3].[CH2:38]([O:41][C:42]([NH:44][CH2:45][CH2:46][CH2:47][I:48])=[O:43])[CH:39]=[CH2:40]>CN(C)C=O>[I-:48].[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH2:9][C@H:8]1[CH2:31][CH2:32][N+:33]1[CH:37]=[CH:36][N:35]([CH2:47][CH2:46][CH2:45][NH:44][C:42]([O:41][CH2:38][CH:39]=[CH2:40])=[O:43])[CH:34]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 19971504HCID 19971504, compoundHCID 53914303HCID 53914303, compound

Product 1

HCID 86750489HCID 86750489, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(imidazol-1-yl)ethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (7.00 g) in dimethylformamide (35 ml) was added 3-allyloxycarbonylamino-l-iodopropane (4.26 g) and the solution was warmed to 50° C. After stirring at the same temperature for 8 hours, the solution was cooled to room temperature. The solvent was evaporated and the residue was washed with diisopropyl ether (175 ml×5) to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-[2-[3-{3-(allyloxycarbonylamino)propyl}-1-imidazolio]ethyl]-pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (10.4 g) as a light brown paste. This compound was immediately used as the starting compound for the next step.

Workup

  1. temperaturethe solution was cooled to room temperature
  2. customThe solvent was evaporated
  3. washthe residue was washed with diisopropyl ether (175 ml×5)

Sources & evidence

ORD record
ord-2c4e411bdc08463cb5ebb55c30ab8b17
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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