Nitrogen → HCID 67958736, compound

HRID 527241Notes

Reaction equation

HRID 527241 reaction equation
N#N.[C:3]([O:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18][O:19][Si](C(C)(C)C)(C)C)[O:16][CH:17]=2)[CH2:12][CH2:11]1)(=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(=O)OCC>[C:3]([O:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18][OH:19])[O:16][CH:17]=2)[CH2:11][CH2:12]1)(=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 947NitrogenHCID 2724141Tetrabutylammonium FluorideHCID 86698884HCID 86698884, compound

Product 1

HCID 67958736HCID 67958736, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(2-(((tert-butyldimethylsilyl)oxy)methyl)oxazol-4-yl)cyclopropyl pivalate (450 mg, 1.27 mmol) in THF (13.0 mL) at 0° C. was treated with TBAF (2.55 ml of a 1M solution in THF, 2.55 mmol) and the reaction mixture was stirred at 0° C. for 30 min. The reaction mixture was diluted with EA (30 mL), the layers were separated and the org. layer was washed sequentially with sat. aq. NH4Cl and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a colorless oil: TLC: rf (1:1 hept-EA)=0.29. LC-MS-conditions 06: tR=0.69 min, [M+H]+=240.11.

Workup

  1. customthe layers were separated
  2. washlayer was washed sequentially with sat. aq. NH4Cl and brine
  3. dry with materiallayer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (1:1 hept-EA)

Sources & evidence

ORD record
ord-7d07c1a25fa24f028e856dda94b08cee
Source dataset
uspto-grants-2016_05
Patent number
US09346793B2

Reaction notes

Loading…