Nitrogen → HCID 66819931, compound

HRID 1044773Notes

Reaction equation

HRID 1044773 reaction equation
N#N.[Si]([O:10][CH2:11][C:12]1[O:13][CH:14]=[C:15]([C:17]2([CH3:22])[O:21][CH2:20][CH2:19][O:18]2)[N:16]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C1COCC1>[CH3:22][C:17]1([C:15]2[N:16]=[C:12]([CH2:11][OH:10])[O:13][CH:14]=2)[O:21][CH2:20][CH2:19][O:18]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 66820233HCID 66820233, compound

Product 1

HCID 66819931HCID 66819931, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 2-{[(tert-butyldimethylsilyl)oxy]methyl}-4-(2-methyl-[1,3]dioxolan-2-yl)oxazole (3.50 g, 11.69 mmol) in dry THF (70 mL) was treated at 0° C. with TBAF (15.2 mL of a 1M solution in THF, 15.20 mmol). The reaction mixture was stirred at 0° C. for 1 h. Sat. aq. NH4Cl was added, the layers separated and the aq. layer extracted with EA. The combined org. extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (2:3 to 1:0 EA-Hept) gave the title compound as a pale yellow oil. TLC: rf (EA)=0.20. LC-MS-conditions 01: tR=0.45 min, [M+H]+=186.00.

Workup

  1. customthe layers separated
  2. extractionthe aq. layer extracted with EA
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by FC (2:3 to 1:0 EA-Hept)

Sources & evidence

ORD record
ord-564d9def285d4831b777512eafc04943
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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