4-Methylmorpholine → N-(1,1-Dimethylethyl)-N'-(4-hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)-N'-(phenylmethyl) Urea

HRID 2393971Notes

Reaction equation

HRID 2393971 reaction equation
Cl.[OH:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:5](=[O:15])[C:4]=1[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN1CCOCC1.[C:31]([N:35]=[C:36]=[O:37])([CH3:34])([CH3:33])[CH3:32]>C(OCC)(=O)C>[CH3:32][C:31]([NH:35][C:36]([N:16]([C:4]1[C:5](=[O:15])[O:6][C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:8][C:3]=1[OH:2])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:37])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62412tert-Butyl isocyanateHCID 1317208334-hydroxy-6-phenyl-3-(phenylmethyl)amino-2H-pyran-2-one, monohydrochloride

Product 1

HCID 54718671N-(1,1-Dimethylethyl)-N'-(4-hydroxy-2-oxo-6-phenyl-2H-pyran-3-yl)-N'-(phenylmethyl) Urea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-hydroxy-6-phenyl-3-(phenylmethyl)amino-2H-pyran-2-one, monohydrochloride (0.153 mmol) in ethyl acetate (10 ml) was added N-methylmorpholine (2.0 ml) and tert-butyl isocyanate (2.0 ml). The reaction was allowed to stir for 2.5 hrs and then quenched by dilution with ethyl acetate. The organic layer was washed with 5% citric acid and saturated sodium chloride and was dried over anhydrous magnesium sulfate. After evaporation of the solvents in vacuo the crude product was purified by column chromatography (silica gel-230 to 400 mesh) using 5% methanol in dichloromethane as eluents. 1H NMR (250 MHz, DMSO-d6) δ 1.24 (s, 9H), 4.47 (dd, 2 H), 5.45 (bs, 1 H), 7.23 (m, 5 H), 7.51 (m, 3 H), 7.75 (m, 2 H).

Workup

  1. customquenched by dilution with ethyl acetate
  2. washThe organic layer was washed with 5% citric acid and saturated sodium chloride
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customAfter evaporation of the solvents in vacuo the crude product
  5. customwas purified by column chromatography (silica gel-230 to 400 mesh)

Sources & evidence

ORD record
ord-4b27a6cedb684753b802ba12fa591c46
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

Loading…