Triethylamine → 3-{[(1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one

HRID 2056760Notes

Reaction equation

HRID 2056760 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31]O)=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[H-].[Na+].[O:47]1[CH2:51][CH2:50][NH:49][C:48]1=[O:52].S([O-])(=O)(=O)C>C(OCC)C.O.C(OCC)(=O)C>[Si:1]([O:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][N:49]3[CH2:50][CH2:51][O:47][C:48]3=[O:52])=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 6

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 739492-OxazolidinoneHCID 85257MethanesulfonateHCID 69310633[(1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methanol

Product 1

HCID 693083913-{[(1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of [(1S)-1-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methanol (0.30 g, 0.67 mmol) in dry diethyl ether (5 mL) and triethylamine (0.11 mL, 0.80 mmol) was added methanesulfonyl chloride (0.057 mL, 0.74 mmol), and the mixture stirred for 2 h under nitrogen. In a separate flask, sodium hydride (60% suspension in oil) (0.107 g, 2.68 mmol) was added to a stirred solution of 1,3-oxazolidin-2-one (0.175 g, 2.1 mmol) and the mixture heated at 50° C. for 2 h. To this solution was added the filtered solution of the mesylate and the mixture heated at 50° C. with stirring for a further 1.5 h, then stirred at room temperature overnight. Ethyl acetate and water were added to the reaction, the organic layer washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica, eluting with ethyl acetate/hexane (1:99 to 60:40), to yield the title compound.

Workup

  1. temperaturethe mixture heated at 50° C.
  2. stirringwith stirring for a further 1.5 h
  3. stirringstirred at room temperature overnight
  4. washthe organic layer washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash chromatography on silica
  9. washeluting with ethyl acetate/hexane (1:99 to 60:40)

Sources & evidence

ORD record
ord-5db8bdfe0c314adabbfa72bc21a5e55a
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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