Cesium carbonate → HCID 118208680, compound

HRID 595200Notes

Reaction equation

HRID 595200 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([O:10][CH2:11][C@:12]2([CH3:15])[CH2:14][O:13]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[I:24][C:25]1[CH:26]=[N:27][NH:28][CH:29]=1>CN(C=O)C.CCOC(C)=O>[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([O:10][CH2:11][C@:12]([OH:13])([CH3:15])[CH2:14][N:27]2[CH:26]=[C:25]([I:24])[CH:29]=[N:28]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 770224-IodopyrazoleHCID 147239Oxiranemethanol, 2-methyl-, 4-nitrobenzoate, (2S)-

Product 1

HCID 118208680HCID 118208680, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-(2-Methyloxiran-2-yl)methyl 4-nitrobenzoate (2.0 g, 8.4 mmol) and cesium carbonate (4.12 g, 12.7 mmol) were added to a solution of 4-iodo-1H-pyrazole (1.64 g, 8.43 mmol) in DMF (30 mL). The mixture was stirred at room temperature for 14 h, then diluted with EtOAc, and washed with hydrochloric acid (1N). The organic layers were separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-60% EtOAc/Hexane) to afford (S)-2-hydroxy-3-(4-iodo-1H-pyrazol-1-yl)-2-methylpropyl 4-nitrobenzoate. MS ESI calc'd. for C14H15IN2O5 [M+H]+ 432. found 432.

Workup

  1. washwashed with hydrochloric acid (1N)
  2. customThe organic layers were separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (0-60% EtOAc/Hexane)

Sources & evidence

ORD record
ord-0e2d3d04db744109872979ba55f1d0c1
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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