Potassium bis(trimethylsilyl)amide → HCID 11619752, compound

HRID 1994464Notes

Reaction equation

HRID 1994464 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C([O:18][C:19](=[O:52])[N:20]([CH2:43][CH:44](O)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=1)[CH2:21][C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=1[C:32]1[CH:37]=[C:36]([CH:38]([CH3:40])[CH3:39])[CH:35]=[CH:34][C:33]=1[O:41][CH3:42])C1C=CC=CC=1>C1(C)C=CC=CC=1.C1COCC1>[CH:38]([C:36]1[CH:35]=[CH:34][C:33]([O:41][CH3:42])=[C:32]([C:23]2[CH:24]=[CH:25][C:26]([C:28]([F:30])([F:29])[F:31])=[CH:27][C:22]=2[CH2:21][N:20]2[CH2:43][CH:44]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=3)[O:18][C:19]2=[O:52])[CH:37]=1)([CH3:40])[CH3:39]

Participants

5

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 66716615HCID 66716615, compound

Product 1

HCID 11619752HCID 11619752, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of potassium bis(trimethylsilyl)amide (464 μL of a 0.5M solution in toluene, 0.232 mmol) was added dropwise to a stirred solution of benzyl(2-hydroxy-2-pyridin-2-ylethyl){[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (134.3 mg, 0.232 mmol) in dry THF (10 mL) at room temperature under N2. After stirring at room temperature for 1 h, the reaction was quenched with saturated NH4Cl (10 mL) and extracted with EtOAc (3×20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 25×160 mm, 0-70% EtOAc in hexanes gradient) to afford 3-{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-5-pyridin-2-yl-1,3-oxazolidin-2-one. Rf=0.58 (50% EtOAc/hexanes). LCMS calc.=471.19; found=471.2 (M+1)+.

Workup

  1. customthe reaction was quenched with saturated NH4Cl (10 mL)
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThis was purified by flash chromatography (Si, 25×160 mm, 0-70% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-5fac2c6bc2cd4a4c85bd394b5ebc23b5
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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