Potassium bis(trimethylsilyl)amide → HCID 11619752, compound

HRID 1028493Notes

Reaction equation

HRID 1028493 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[OH:11][CH:12]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1)[CH2:13][N:14]([CH2:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1[C:36]1[CH:41]=[C:40]([CH:42]([CH3:44])[CH3:43])[CH:39]=[CH:38][C:37]=1[O:45][CH3:46])[C:15](=[O:24])OCC1C=CC=CC=1>C1(C)C=CC=CC=1.C1COCC1>[CH:42]([C:40]1[CH:39]=[CH:38][C:37]([O:45][CH3:46])=[C:36]([C:27]2[CH:28]=[CH:29][C:30]([C:32]([F:33])([F:35])[F:34])=[CH:31][C:26]=2[CH2:25][N:14]2[CH2:13][CH:12]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=3)[O:11][C:15]2=[O:24])[CH:41]=1)([CH3:43])[CH3:44]

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-259191bc857040de8e9592debb49407f
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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