Triethylsilane → HCID 57435089, compound

HRID 1366901Notes

Reaction equation

HRID 1366901 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][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH: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][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:17]=1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 57435088HCID 57435088, compound

Product 1

HCID 57435089HCID 57435089, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (0.776 mL, 4.87 mmol) was added to a stirring, room temperature solution of 43 (0.5266 g, 1.57 mmol) in trifluoroacetic acid (TFA) (3.74 mL, 0.42 M) under N2. After stirring at room temperature for 4 hours, 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: 0 to 11 min, 35:65 H2O:CH3CN. 11.5-20 min, 35:65 to 0:100H2O:CH3CN; 20 mL/min.; λ=254 nM; 200 mg/mL, 0.7 mL/injection. 0.2455 g (48.7%) of 44 was obtained as a fluffy white solid. (Note: An undesired impurity has a retention time of 12.062 min by HPLC). 1H (CDCl3, 400 MHz): δ 9.27 (1H, broad s), 7.34-7.26 (2H, m), 7.24-7.17 (3H, m), 6.81 (1H, s), 6.75 (1H, s), 4.33 (2H, q, J=7.1 Hz), 2.67 (2H, t, J=7.8 Hz), 2.53 (2H, t, J=7.8 Hz), 1.93 (2H, quint, J=7.8 Hz), 1.37 (3H, t, J=7.1 Hz) ppm. 13C (CDCl3, 100 MHz): δ 161.34, 142.31, 128.40, 128.22, 125.99, 125.64, 122.47, 120.73, 114.82, 60.17, 35.33, 32.47, 26.17, 14.41 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 14.41; CH2 carbons: 60.17, 35.33, 32.47, 26.17; CH carbons: 128.40, 128.22, 125.64, 120.73, 114.82 ppm. HPLC: 11.140 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. custom0 to 11 min, 35:65 H2O
  8. custom11.5-20 min, 35:65

Sources & evidence

ORD record
ord-895eb8cfd3d0475c8d7092707b66c155
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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