Cesium carbonate → HCID 86612855, compound

HRID 1782032

Reaction equation

HRID 1782032 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([NH:13][CH3:14])=[O:12].[N+](C1C=C(S(O[CH2:28][C@@H:29]2[CH2:31][O:30]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:10][C:11]([NH:13][CH3:14])=[O:12])=[C:2]([O:1][CH2:28][C@@H:29]2[CH2:31][O:30]2)[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 690173522-(2-hydroxy-4-methoxyphenyl)-N-methylacetamide

Product 1

HCID 86612855HCID 86612855, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-hydroxy-4-methoxyphenyl)-N-methylacetamide (15 mg, 0.076 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (20 mg, 0.076 mmol) and Cs2CO3 (30 mg, 0.091 mmol) in DMF (1.5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-100% ethyl acetate in petroleum spirit) to give the subtitled compound (18 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (0-100% ethyl acetate in petroleum spirit)

Sources & evidence

ORD record
ord-bdf2fce010bd419281858860233fc2c2
Source dataset
uspto-grants-2009_03
Patent number
US07498338B2

Linked notes

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