Triethylamine → HCID 68694568, compound

HRID 1710933Notes

Reaction equation

HRID 1710933 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:23]=[CH:22][C:14]([CH2:15][N:16]4[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17]4)=[CH:13][CH:12]=3)[S:10][C:3]=12.[Si:24](OS(C(F)(F)F)(=O)=O)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCN(CC)CC.CO.CCOC(C)=O>C1COCC1>[Si:24]([O:21][C@H:18]1[CH2:19][CH2:20][N:16]([CH2:15][C:14]2[CH:13]=[CH:12][C:11]([C:9]3[S:10][C:3]4[C:4](=[N:5][CH:6]=[CH:7][C:2]=4[Cl:1])[CH:8]=3)=[CH:23][CH:22]=2)[CH2:17]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 21584119Ethylacetate methanolHCID 59424545HCID 59424545, compound

Product 1

HCID 68694568HCID 68694568, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 99 (0.5 g, 1.45 mmol) in dry THF (7 ml) at 0° C. was added TBDMSOTf (0.5 ml, 2.2 mmol) and the reaction mixture was stirred for 20 min. Et3N (0.61 ml, 4.4 mmol) was added and mixture was stirred at the same conditions for another hour, quenched by the addition of water (˜2 ml) and concentrated to dryness. The remained solid was partitioned between EtOAc and water. Organic phase was collected, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography, eluents EtOAc/hexane (1:1) then MeOH/EtOAc (5:95) to afford title compound 100 (637 mg, 96% yield) as a white solid. MS (m/z): 459.2/461.2 (M+H).

Workup

  1. stirringmixture was stirred at the same conditions for another hour
  2. customquenched by the addition of water (˜2 ml)
  3. concentrationconcentrated to dryness
  4. customThe remained solid was partitioned between EtOAc and water
  5. customOrganic phase was collected
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography, eluents EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-ff8b8c82f56a440c832a81d78713d584
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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