Methanol → HCID 136341186, compound

Participants

Reaction Steps

A solution of the product of stage (a) (2.0 g, 2.66 mmol) and 10% palladium on carbon (250 mg, Aldrich) in glacial acetic acid (250 ml) was shaken on a Parr Hydrogenator under 30 to 35 psi H2 for 5 hours. Reaction progress was monitored by TLC (silica gel, CH2Cl2 :MeOH/9:1). The catalyst was removed by filtration (Millipore Prefilter). Dilution of the filtrate with ether caused the product to separate as an oil. After 14 hours at 5° C., the supernatant was decanted from a colourless gum, which was dried under high vacuum to a white foam. The foam was dissolved in water (20 ml), filtered, and freeze-dried to a white foam; yield, 1.3 g (79%). H-NMR (DMSO-d6) 7.79(3,1H), 6.49(br s,2H), 5.41(s,2H), 3.9-4.2(m,4H), 3.10(d,1H), 3.06(d,1H), 1.9 (HOAc), 1.5(m,1H), 1.34(m,4H), 1.1(m,4H); 0.73-0.78(m,12H), 13C-NMR (DMSO-d6) 156.80, 153.96, 151.30, 137.47, 116.30, 73.41, 70.78, 62.88, 62.57, 58.15, 24.18, 21.28, 15.33, 15.28, 11.33; HPLC (Versapack C-18; 30% MeOH (aq.)/0.1% TFA) 1 peak, k'=1.22; UV max (H2O) 251 nm (12,000). MS (positive ion/Cl) m/z 482. Anal. Calcd. for C21H 35 N7O6.2HOAc:1H2O: C,48.46; H,7.32; N,15.82. Found: C,48.52; H,7.3; N,15.75.

Provenance & Evidence