Cesium carbonate → HCID 86596905, compound

HRID 1455460Notes

Reaction equation

HRID 1455460 reaction equation
[CH:1]([O:4][CH:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:29])[C@@H:13]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:14][CH2:15]SC)[C@H:7]([CH2:30][S:31]([CH:34]([CH3:36])[CH3:35])(=[O:33])=[O:32])[CH2:6]1)([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[CH:1]([O:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:12]2=[O:29])[C@H:7]([CH2:30][S:31]([CH:34]([CH3:35])[CH3:36])(=[O:32])=[O:33])[CH2:6]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 86596906HCID 86596906, compound

Product 1

HCID 86596905HCID 86596905, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of benzyl (S)-1-((1S,2R)-4-isopropoxy-2-(isopropylsulfonyl methyl)cyclohexylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate (2.8 g, 5.16 mMol) was stirred at rt. After 24 h the solution was evaporated. The residue was redissolved in CH2Cl2 and evaporated. This process was repeated four more times. The residue was dried in vacuo to get a yellow foamy solid. This solid was dissolved in DMSO and treated with Cs2CO3 (3.36 g, 10.32 mMol). The reaction was set to stir at rt. After 4 h, the reaction was quenched with saturated aq. NH4Cl. Extracted the reaction mixture with EtOAc three times. The combined organic layer was washed with brine twice. It was dried (MgSO4), filtered, concentrated and chromatographed to get benzyl (S)-1-((1S,2R,4R)-4-isopropoxy-2-(isopropylsulfonylmethyl)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate A (faster isomer, 0.41 g, oil) and benzyl (S)-1-((1S,2R,4R)-4-isopropoxy-2-(isopropylsulfonylmethyl)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate B (slower isomer, 0.62 g, white solid).

Workup

  1. customAfter 24 h the solution was evaporated
  2. dissolutionThe residue was redissolved in CH2Cl2
  3. customevaporated
  4. customThe residue was dried in vacuo
  5. customto get a yellow foamy solid
  6. customthe reaction was quenched with saturated aq. NH4Cl
  7. extractionExtracted the reaction mixture with EtOAc three times
  8. washThe combined organic layer was washed with brine twice
  9. dry with materialIt was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customchromatographed

Sources & evidence

ORD record
ord-b60e3840a66c4e60b6c0bda5ed02f8b4
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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