Ninhydrin → HCID 23292698, compound

Participants

Reaction Steps

To BHA resin (obtained from 7.0 g BHA resin hydrochloride after neutralization with 10% Et3N in CH2Cl2 and washing with CH2Cl2, 7.77 mmMol) was added a solution of the above 3-[dimethyl-4-(hydroxymethyl)phenylsilyl]propionic acid (2.36 g, 9.9 mmol) in DMF (30 mL). To this were added HOBt (2.7 g, 20 mmol) and DCC (2.1 g, 9.9 mmol). The reaction was shaken for 16 h, washed with DMF (2×30 mL), (1:1) CHCl3 :MeOH (2×30 mL), CH2Cl2 (2×30 mL), hexane (30 mL) and dried under vacuum for 24 h to give resin 2-Scheme 6. (8.66 g, 0.90 mmol/g): negative ninhydrin test; (Kaiser et al., Anal. Biochem. 1970, 34, 594-598). MAS 1H NMR (500 Mhz) δ 0.20 (6H, Si(CH3)2 's), 1.05 (2H, CH2CON), 2.10 (2H, SiCH2C), 2.80 (1H, HO), 4.52 (2H, OCH2 --Ar), 7.22, 7.40 (4H, ArH's).

Provenance & Evidence