Methyl fluorosulfate → HCID 178459466, compound

HRID 975728Notes

Reaction equation

HRID 975728 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][CH:35]=[N:34]1)=[O:6])[CH:2]=[CH2:3].[F:38][S:39]([O:42][CH3:43])(=[O:41])=[O:40]>ClCCl>[F:38][S:39]([O-:42])(=[O:41])=[O:40].[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[N:34]([CH3:43])[CH:35]=[CH:36][CH:37]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 57286900HCID 57286900, compound

Product 1

HCID 178459466HCID 178459466, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(pyrazol-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 (10.49 g) in dichloromethane (150 ml) was added methyl fluorosulfonate (2.33 ml) with stirring under ice-cooling. The mixture was stirred for 1.5 hours at the same temperature. The mixture was evaporated in vacuo to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(2-methyl-1-pyrazolio)ethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate fluorosulfonate (12.75 g). This compound was immediately used as the starting compound for the next step.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1.5 hours at the same temperature
  3. customThe mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-6c87ec0db322464ca23cf1993b84e5ad
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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