Triethylamine → HCID 86687115, compound

HRID 2285104Notes

Reaction equation

HRID 2285104 reaction equation
FC(F)(F)S([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])(=O)=O.[CH3:19][O:20][C:21]([C@:23]1([CH2:29]O)[CH2:27][CH2:26][CH2:25][N:24]1[CH3:28])=[O:22].CCN(CC)CC>C(Cl)Cl>[CH3:19][O:20][C:21]([C@:23]1([CH2:29][O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])[CH2:27][CH2:26][CH2:25][N:24]1[CH3:28])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 86687114HCID 86687114, compound

Product 1

HCID 86687115HCID 86687115, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triisopropylsilyl trifluoromethanesulfonate (11.7 g, 38.1 mmol) was added to a solution of Intermediate 85e (2.20 g, 12.7 mmol) and Et3N (12.8 g, 127 mmol) in DCM (100 mL) at 0° C., then the mixture stirred at RT for 30 min. The mixture was diluted with DCM and washed with 10% aq. K2CO3 solution, water, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by FCC, using 0-5% [2M NH3 in MeOH] in DCM, to give the title compound as a pale yellow solid (2.51 g, 65%). 1H NMR (400 MHz, CDCl3): 0.97-1.15 (21H, m), 1.72-1.96 (2H, m), 2.23-2.35 (2H, m), 2.46 (3H, s), 2.89-2.99 (2H, m), 3.69 (3H, m), 4.12-4.22 (2H, m).

Workup

  1. washwashed with 10% aq. K2CO3 solution, water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-c508853015cd44b6acfd46f0a8245272
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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