Nitrogen → HCID 86649487, compound

HRID 1044744Notes

Reaction equation

N#N.[C:3]([Si:7]([CH3:17])([CH3:16])[O:8][CH:9]([C:11]1[O:12][CH:13]=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].[Li]C(C)(C)C.CN(C)[CH:25]=[O:26].[NH4+].[Cl-]>C1COCC1.CCCCC.O>[C:3]([Si:7]([CH3:17])([CH3:16])[O:8][CH:9]([C:11]1[O:12][C:13]([CH:25]=[O:26])=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: -40 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazole (733 mg, 3.22 mmol) in dry THF (16 mL) was added tert-BuLi (2.62 mL of a 1.6 M solution in pentane, 4.19 mmol) at −78° C. The reaction mixture was then stirred for 1 h at −40° C. and cooled to −78° C. before N,N-dimethylformamide (0.49 mL, 6.44 mmol) was added dropwise. The reaction mixture was allowed to warm up to rt over a period of 1 h and stirred at this temperature for 2 h. Water (30 mL) and sat. aq. NH4Cl (20 mL) were added, the layers separated and the aq. layer extracted with EA (2×30 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a colorless oil. TLC:rf (4:1 hept-EA)=0.33. LC-MS-conditions 02: tR=1.08 min; [M+H]+=256.37.

Workup

additionwas added dropwise
temperatureto warm up to rt over a period of 1 h
stirringstirred at this temperature for 2 h
customthe layers separated
extractionthe aq. layer extracted with EA (2×30 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvent was removed under reduced pressure
customPurification of the residue by FC (4:1 hept-EA)

Sources & evidence

ORD record: ord-7bc31a00e8364d9c96fb5b778582560b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563714B2

Reaction notes

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