Methyl triflate → HCID 86750487, compound

HRID 975725Notes

Reaction equation

HRID 975725 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]=[C:36]([C:38]#[N:39])[N:35]=[CH:34]1)=[O:6])[CH:2]=[CH2:3].[F:40][C:41]([F:48])([F:47])[S:42]([O:45]C)(=[O:44])=[O:43]>ClCCl>[F:40][C:41]([F:48])([F:47])[S:42]([O-:45])(=[O:44])=[O:43].[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]=[C:36]([C:38]#[N:39])[N:35]([CH3:41])[CH:34]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 57073737HCID 57073737, compound

Product 1

HCID 86750487HCID 86750487, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(4-cyanoimidazol-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 (7.56 g) in dichloromethane (110 ml) was added methyl trifluoromethanesulfonate (3.1 ml) at room temperature and the solution was stirred at the same temperature for 30 minutes. The solvent was evaporated to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(4-cyano-3-methyl-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 trifluoromethanesulfonate (10.4 g) as a yellow paste. This compound was immediately used as the starting compound for the next step.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9cbf3cbab03f4a329bd812b8441454ce
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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