Nitrogen → N-{4-Methoxy-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide

HRID 270058Notes

Reaction equation

HRID 270058 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:13])[CH3:12].[O:14]1[CH2:16][C@H:15]1[CH2:17]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].N#N>CN(C=O)C.O.C(OCC)(=O)C>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([NH:10][C:11](=[O:13])[CH3:12])=[C:2]([O:1][CH2:17][C@@H:15]2[CH2:16][O:14]2)[CH:7]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 41051392'-Hydroxy-4'-methoxyacetanilide

Product 1

HCID 71570340N-{4-Methoxy-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamideYield 122.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(2-Hydroxy-4-methoxyphenyl)acetamide (18.12 g, 0.1 mol) and (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (25.92 g, 0.1 mol) were dissolved in dry DMF (75 mL) and stirred under nitrogen (N2) on an ice-bath. Cesium carbonate (35.8 g, 0.1 mol) was added and the stirring under N2 was continued at ambient temperature overnight. The mixture was poured into ethyl acetate (1 L) and water (250 mL). The organic phase was washed with water (3×250 mL), dried over Na2SO4, filtered and concentrated in vacuo to give an orange solid crude product (29 g), which was recrystallized from ethanol (100 mL) and washed with ether to give white crystals. More white crystals were obtained from the mother liquor, after evaporation and recrystillazition from 2-propanol. Total yield 15 g is (63%).

Workup

  1. washThe organic phase was washed with water (3×250 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a60ebe705e74ab0bdc7477ccc06a412
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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