Ethyl Acetate → HCID 178435578, compound

HRID 1647041Notes

Reaction equation

HRID 1647041 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[NH:9][C:5]=2[C:4]=1[N:13]1[CH2:17][CH:16]([CH2:18]I)[O:15][C:14]1=[O:20])[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+].C(OCC)(=O)C>CC(C)=O.O>[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[NH:9][C:5]=2[C:4]=1[N:13]1[CH2:17][CH:16]([CH2:18][N:21]=[N+:22]=[N-:23])[O:15][C:14]1=[O:20])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 178435576HCID 178435576, compound

Product 1

HCID 178435578HCID 178435578, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A mixture of (±)-3-(5'-1-ethyl-2-methylbenzimidazolyl)-5-(iodomethyl)oxazolidin-2-one (XXXVIII, EXAMPLE 69, 0.531 g) and sodium azide (0.618 g) are stirred in acetone/water (2/1, 30 ml) at reflux under a nitrogen overnight. After this time the mixture is poured into ethyl acetate and the layers are separated. The aqueous layer is then extracted with ethyl acetate (2×). All organic layers are combined, dried over magnesium sulfate and concentrated under reduced pressure to give an oil. A small amount of the crude product (oil) is purified on a silica preparative plate (20 cm×20 cm, 1000μ). The plate is eluted in methanol/ethyl acetate (10/90, 5×) to give the title compound as an oil; NMR (CDCl3, 300 MHz) 7.70, 7.53, 7.30, 4.80, 4.15, 3.89, 3.70, 3.60, 2.61 and 3.40 δ; CMR (CDCl3, 75.47 MHz) 13.62, 14.78, 38.62, 48.42, 53.05, 70.60, 109.29, 114.99, 132.1, 132.72, 142.3, 152.8 and 154.9 δ; MS (m/e) 300, 272, 227, 212, 200, 186, 172, 160, 159, 145, 131, 117, 104, 90 and 77; exact mass calcd for C14H16N6O2 =300.1335, found: 300.1333.

Workup

  1. temperatureat reflux under a nitrogen overnight
  2. customthe layers are separated
  3. extractionThe aqueous layer is then extracted with ethyl acetate (2×)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. customA small amount of the crude product (oil) is purified on a silica preparative plate (20 cm×20 cm, 1000μ)
  8. washThe plate is eluted in methanol/ethyl acetate (10/90, 5×)

Sources & evidence

ORD record
ord-80ae221fd6c146e08f8704465748c92a
Source dataset
uspto-grants-1993_01
Patent number
US05182403

Reaction notes

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