Cesium carbonate → HCID 67182479, compound

HRID 1171459Notes

Reaction equation

HRID 1171459 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:32][CH2:33]SC)[C:13]([NH:15][C@H:16]1[CH2:22][CH2:21][C@@H:20]2[CH2:23][C@H:17]1[C:18](=[O:31])[N:19]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+]>IC.CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:32][CH2:33][N:15]([C@H:16]2[CH2:22][CH2:21][C@@H:20]3[CH2:23][C@H:17]2[C:18](=[O:31])[N:19]3[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13]1=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 21074905(1R,2S,5R)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-4-(methylthio)butanamido)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate

Product 1

HCID 67182479HCID 67182479, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6328Methyl iodideSolvent

Procedure

(1R,2S,5R)-tert-Butyl 2-((S)-2-(benzyloxycarbonylamino)-4-(methylthio)butanamido)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (5.1 g) was dissolved in iodomethane (40 mL). The resulting solution was stirred at rt for 12 h before being concentrated in vacuo. The residue was dissolved in methylene chloride, and the resulting solution was concentrated; this was repeated to afford the salt. This material was dissolved in DMF (30 mL) and the solution was charged with Cs2CO3 (6.6 g). After 12 h, the reaction was partitioned between EtOAc and brine. The organic phase was dried (MgSO4), filtered, and concentrated. The resulting residue was purified by flash chromatography to afford (1R,2S,5R)-tert-butyl 2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (2.0 g). MS found: (M+H)+=458.6.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. concentrationthe resulting solution was concentrated
  4. customto afford the salt
  5. waitAfter 12 h
  6. customthe reaction was partitioned between EtOAc and brine
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b4d67a92e9724a2eaeb477a12bbd2161
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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