Cesium carbonate → HCID 86601483, compound

HRID 270090Notes

Reaction equation

HRID 270090 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.[OH:19][C:20]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[CH:27]=[CH:26][C:21]=1[C:22]([NH:24][CH3:25])=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][O:30][C:28]2[CH:27]=[CH:26][C:21]([C:22]([NH:24][CH3:25])=[O:23])=[C:20]([O:19][CH2:1][C@:2]3([CH3:5])[CH2:4][O:3]3)[CH:29]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 68959972HCID 68959972, compoundHCID 86597620HCID 86597620, compound

Product 1

HCID 86601483HCID 86601483, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [(2S)-2-methyloxiran-2-yl]methyl3-nitrobenzenesulfonate (133 mg, 0.487 mmol), 2-hydroxy-4-[(4-methoxybenzyl)oxy]-N-methylbenzamide (140 mg, 0.487 mmol) and cesium carbonate, Cs2CO3, (198 mg, 0.608 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 and concentrated. The residue was purified by silica gel flash chromatography (0-60% ethyl acetate in petroleum ether) to give the subtitled compound (130 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 (0-60% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-202b8d191bd04c4b955e5772e1d7b609
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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