Nitrogen → HCID 131730010, compound

HRID 2065079Notes

Reaction equation

HRID 2065079 reaction equation
N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:16])([CH3:15])[C:10]1[O:11][CH:12]=[CH:13][N:14]=1)([CH3:6])([CH3:5])[CH3:4].C([Li])(C)(C)C.CN(C)[C:24](=[O:26])[CH3:25].[NH4+].[Cl-]>C1COCC1.CCCCC.O>[C:3]([SiH2:7][O:8][C:9]([CH3:16])([CH3:15])[C:10]1[O:11][C:12]([C:24](=[O:26])[CH3:25])=[CH:13][N:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

9

Reactant 5

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 1317300112-(Tert-butyl-dimethyl-silanyloxymethyl)-oxazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 131730010HCID 131730010, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazole (480 mg, 2.25 mmol) in dry THF (11.0 mL) was treated at −78° C. with a solution of t-butyllithium (1.83 mL of a 1.6M solution in pentane, 2.93 mmol) while keeping the temperature below −70° C. The reaction mixture was then stirred for 1 h at −40° C. N,N-Dimethyl-acetamide (0.42 mL, 4.50 mmol) was added dropwise to the reaction mixture at −78° C. and the reaction mixture was allowed to warm to rt and stirred for 2 h at rt. Water (20 mL) followed by sat. aq. NH4Cl (15 mL) were added. The aq. layer was extracted with EA (2×20 mL) and the combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (4:1 hept-EA)=0.25. LC-MS-conditions 02: tR=1.05 min; [M+H]+=256.47.

Workup

  1. customthe temperature below −70° C
  2. temperatureto warm to rt
  3. stirringstirred for 2 h at rt
  4. additionwere added
  5. extractionThe aq. layer was extracted with EA (2×20 mL)
  6. washextracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customPurification of the residue by FC (4:1 hept-EA)

Sources & evidence

ORD record
ord-57ee188397ca46c5a5c948d3fdd351b3
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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