1,1'-Carbonyldiimidazole → HCID 69384067, compound

HRID 916812Notes

Reaction equation

HRID 916812 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Si:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH:28]([NH:30][CH2:31][C@@H:32]([C:34]2[CH:45]=[CH:44][C:37]3[O:38][C:39]([CH3:43])([CH3:42])[O:40][CH2:41][C:36]=3[CH:35]=2)[OH:33])[CH3:29])=[CH:23][CH:22]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C1COCC1>[Si:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][C@@H:28]([N:30]2[CH2:31][C@@H:32]([C:34]3[CH:45]=[CH:44][C:37]4[O:38][C:39]([CH3:43])([CH3:42])[O:40][CH2:41][C:36]=4[CH:35]=3)[O:33][C:1]2=[O:2])[CH3:29])=[CH:25][CH:26]=1)([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 69385001HCID 69385001, compound

Product 1

HCID 69384067HCID 69384067, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1,1′-Carbonyldiimidazole (0.62 g) was added to a solution of (1R)-2-{[2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-methylethyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (0.83 g) in THF (8 ml). The mixture was stirred for 18 h at 20° C. and partitioned between Et2O and water. The organic phase was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified by chromatography on a Biotage (40 g) eluting with cyclohexane-EtOAc (5:1 then 3:1) to give (5R)-3-[(1S)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-methylethyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (0.32 g), LCMS RT=4.17 min and (5R)-3-[(1R)-2-(4-{[tent-butyl(dimethyl)silyl]oxy}phenyl)-1-methylethyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (0.36 g) LCMS RT=4.15 min.

Workup

  1. custompartitioned between Et2O and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography on a Biotage (40 g)
  6. washeluting with cyclohexane-EtOAc (5:1

Sources & evidence

ORD record
ord-402e69ab46854cecbc47a418657cbeb3
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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