Triethylsilane → HCID 57435106, compound

HRID 1434782Notes

Reaction equation

HRID 1434782 reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18](=O)[CH2:19][CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:17]=1)=[O:12])[CH3:9]>FC(F)(F)C(O)=O>[CH2:8]([O:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([CH2:18][CH2:19][CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[CH:17]=1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 57435105HCID 57435105, compound

Product 1

HCID 57435106HCID 57435106, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (4.28 mL, 26.86 mmol) was added to a stirring, room temperature solution of 74 (2.2816 g, 8.66 mmol) in trifluoroacetic acid (TFA) (20.6 mL, 0.42 M) under N2. When the reaction was judged complete by HPLC, the TFA was removed under vacuum, and the crude product was taken up in EtOAc, washed with brine, dried with Na2SO4, filtered, concentrated, and purified by preparative reverse phase HPLC with the following conditions: 30:70 H2O:CH3CN; 20 mL/min.; λ=254 nm. 75 was obtained as a fluffy white solid. 1H (CDCl3, 400 MHz): δ 9.43 (1H, broad s), 6.77 (1H, s), 6.74 (1H, s), 4.32 (2H, q, J=7.1 Hz), 2.46 (2H, t, J=7.6 Hz), 1.83-1.71 (3H, m), 1.64-1.46 (6H, m), 1.35 (3H, t, J=7.1 Hz), 1.36-1.31 (2H, m), 1.14-1.02 (2H, m) ppm. 13C (CDCl3, 100 MHz): δ 161.46, 126.62, 122.33, 120.74, 114.86, 60.10, 40.00, 35.82, 32.65, 30.14, 26.94, 25.13, 14.39 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 14.39; CH2 carbons: 60.10, 35.82, 32.65, 30.14, 26.94, 25.13; CH carbons: 120.74, 114.86, 40.00 ppm. HPLC: 12.379 min.

Workup

  1. customthe TFA was removed under vacuum
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by preparative reverse phase HPLC with the following conditions
  7. custom75 was obtained as a fluffy white solid
  8. custom12.379 min.

Sources & evidence

ORD record
ord-2919fd6ba1784259bd9d7f5c94d857b2
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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