tert-Butyldimethylsilyl trifluoromethanesulphonate → Tert-butyl (2-((8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methylquinoxalin-2-yl)amino)-2-methylpropyl)carbamate

HRID 1056214Notes

Reaction equation

HRID 1056214 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([NH:14][C:15]([CH3:26])([CH3:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]([CH3:27])=[N:9]2)(=[O:3])[CH3:2].FC(F)(F)S(O[Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])(=O)=O>C(Cl)Cl>[Si:34]([O:3][C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([NH:14][C:15]([CH3:26])([CH3:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[C:10]([CH3:27])=[N:9]2)=[CH2:2])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]

Participants

4

Reactant 2

HCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 89793768HCID 89793768, compound

Product 1

HCID 89793770Tert-butyl (2-((8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methylquinoxalin-2-yl)amino)-2-methylpropyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl (2-((8-acetyl-3-methylquinoxalin-2-yl)amino)-2-methylpropyl)carbamate (339a, 0.78 g, 2.094 mmol), tert-butyldimethylsilyl trifluoromethanesulfonate (0.72 mL, 3.14 mmol), and TEA (0.88 mL, 6.28 mmol) in DCM (21 mL) was stirred at 0° C. for 20 min when the silyl enol ether was observed via lcms. The reaction mixture was diluted with DCM (100 mL), added to a separatory funnel, and washed with saturated aq. NaHCO3 (100 mL) before the organic layer was separated, dried over Na2SO4, and concentrated to give tert-butyl (2-((8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methylquinoxalin-2-yl)amino)-2-methylpropyl)carbamate (339b) as a yellow oil. MS (ESI, pos. ion) m/z: 487.3 (M+1).

Workup

  1. additionadded to a separatory funnel
  2. washwashed with saturated aq. NaHCO3 (100 mL) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-38b7247bf34441d28680282bd7bb0385
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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