Sodium Bisulfate → HCID 178455196, compound

HRID 878624Notes

Reaction equation

HRID 878624 reaction equation
[Si:1]([O:8][CH2:9][CH2:10]/[C:11](=[CH:16]\[NH:17][NH:18][C:19]1[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][N:20]=1)/[C:12](OC)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC([O-])(C)C.[K+].OS([O-])(=O)=O.[Na+]>C(O)C.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[N:17][N:18]([C:19]2[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][N:20]=2)[C:12]=1[OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 516919Sodium BisulfateHCID 23665647Potassium tert-butoxideHCID 86725589HCID 86725589, compound

Product 1

HCID 178455196HCID 178455196, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl (2E)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[2-(4-cyanopyridin-2-yl)hydrazinyl]methylidene]butanoate (3.3 g, 8.77 mmol) in ethanol (50 mL) at 0° C. was added t-BuOK (2.95 g, 26.33 mmol). The reaction mixture was stirred overnight at r.t. It was then cooled to 0° C., diluted with ethyl acetate, and acidified with NaHSO4 (5%) to pH=3. The organic phase was separated and concentrated to a residue which was washed with PE/EA to give 300 mg of the title compound (10%). 1H NMR (400 MHz, CD3OD): δ 0.00 (6H, s), 0.85 (9H, s), 2.49 (2H, d, J=6.4 Hz), 3.74 (2H, d, J=6.4 Hz), 7.48 (1H, dd, J=1.2 Hz, 4.8 Hz), 7.60 (1H, s), 8.57 (1H, d, J=4.8 Hz), 8.61-8.63 (1H, m). [M+H] Calc'd for C17H24N4O2Si, 345; Found, 345.

Workup

  1. temperatureIt was then cooled to 0° C.
  2. customThe organic phase was separated
  3. concentrationconcentrated to a residue which
  4. washwas washed with PE/EA

Sources & evidence

ORD record
ord-aa6c96b52b0f4d599589d8410e3af19d
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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