Cesium carbonate → HCID 87636834, compound

HRID 270083Notes

Reaction equation

HRID 270083 reaction equation
[CH3:1][C@@:2]1([CH2:5]OS(C2C=CC=C([N+]([O-])=O)C=2)(=O)=O)[CH2:4][O:3]1.[CH:19]1([NH:22][C:23](=[O:41])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)=[CH:26][C:25]=2[OH:40])[CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH:19]1([NH:22][C:23](=[O:41])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)=[CH:26][C:25]=2[O:40][CH2:1][C@:2]2([CH3:5])[CH2:4][O:3]2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 68958982HCID 68958982, compoundHCID 86597620HCID 86597620, compound

Product 1

HCID 87636834HCID 87636834, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [(2S)-2-methyloxiran-2-yl]methyl3-nitrobenzenesulfonate (218 mg, 0.797 mmol), N-cyclopropyl-2-hydroxy-4-[(4-methoxybenzyl)oxy]benzamide (250 mg, 0.797 mmol) and cesium carbonate, Cs2CO3, (311 mg, 0.956 mmol) in dimethylformamide (5 mL) was kept on stirring at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulphate, Na2SO4, filtered, concentrated and the residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether) to give the subtitled compound (260 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over sodium sulphate, Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-344d869a6e6b4a1f88b458019e0d0080
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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