Compound 4

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InChIKey GOQJTISYHIQSKD-UHFFFAOYSA-O

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Pd/C 10 wt% (600 mg 0.662 mmol) was added to 3 dissolved in MeOH (55 mL). A slight vacuum was applied to the reaction mixture until boiling of the solvent was observed. The reaction vessel was flushed with H₂, introduced via a balloon, and the mixture stirred vigorously for 1 h under ambient conditions. The mixture was filtered through Celite and evaporated on a rotary evaporator to yield a white crystalline solid; yield (540 mg, 90%), Mp 113-117 ^oC. This compound was employed directly in the next step without further purification. ¹H NMR (500 MHz, CD₂Cl₂): δ = 9.82 (s, 2H, N-H₂), 8.83 (s, 1H, Ar-H), 8.78 (s, 1H, Ar- H), 8.58 (s, 4H, Ar- H), 5.16 (s, 2H, Ar-CH₂), 4.46 (m, 8H, OCH₂CH₃), 3.7-3.4 (m, 20H, OCH₂CH₂O), 3.3 (m, 4H, OCH₂CH₂CH₂CH₂), 1.46 (m, 12H, OCH₂CH₃), 1.26 (m, 4H, OCH₂CH₂CH₂CH₂), 1.12 (m, 8H, OCH₂CH₂CH₂CH₂) ¹³C NMR (125 MHz, CD₂Cl₂): δ = 165.5, 164.5, 136.2, 135.1, 134.1, 132.7, 132.4, 132.2, 128.5, 72.5, 72.4, 71.8, 71.4, 71.1, 70.6, 62.9, 62.5, 29.9, 28.2, 25.8, 14.8, 14.7. HR-MS (ESI-TOF): Calculated for [M + H]⁺ [C₄₃H₆₆NO₁₄]⁺m/z = 820.4477; found m/z = 820.4445.