Cesium carbonate → HCID 86596880, compound

HRID 1374326Notes

Reaction equation

HRID 1374326 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:35][CH2:36]SC)[C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][C@@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][C@H:17]1[CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])=[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[CH2:35][CH2:36][N:15]([C@H:16]2[CH2:21][CH2:20][C@@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:18][C@H:17]2[CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])[C:13]1=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86596881HCID 86596881, compound

Product 1

HCID 86596880HCID 86596880, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6328Methyl iodideSolvent

Procedure

Tert-butyl (1R,3R,4S)-4-((S)-2-benzyloxycarbonylamino-4-(methylthio)butanamido)-3-(methylsulfonylmethyl)cyclohexylcarbamate (6.9 g) was dissolved in iodomethane (100 mL), and the resulting solution was stirred at rt for 72 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. MS found: (M+H)+=586.5. This material was dissolved in DMF (20 mL) and the solution was charged with Cs2CO3 (12.0 g). After 12 h, the reaction was partitioned between EtOAc and brine. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford tert-butyl (1R,3R,4S)-4-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-3-(methylsulfonylmethyl)cyclohexylcarbamate (2.4 g). MS found: (M+H)+=524.3.

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 in vacuo
  10. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1f057f510a454c708c02cb0338cc84d1
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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