Benzhydrylamine → HCID 178427601, compound

Participants

Reaction Steps

Benzhydrylamine-resin (BHA) (40.44 g, 0.5 mmol/g, 20.22 mmol) was coupled with Boc-Arg(Tos)-OH (34.6 g, 80.7 mmol) in 25% dimethylformamide:methylene chloride [DMF-CH2Cl2 ] (250 ml) with DCC (16.78 g, 81.4 mmol) for 2 hours followed by the addition of 1% diisopropylethylamine and reacted for 0.5 hour longer. The resultant Boc-Arg(Tos)-BHA-resin was washed with CH2Cl2 (3×250 ml), MeOH (3×250 ml), CH2Cl2 (3×250 ml) and dried. The coupling and washing procedures were repeated and an aliquot was hydrolyzed (1 ml of 6M propionic/HCl at 130° C. for 2 hours). Amino acid analysis showed a substitution of 0.35 mmol of Arg per gram of resin. The remaining amino groups were acetylated with Ac2O-pyridine yield: 48.88 g.

Provenance & Evidence