Hydrochloric Acid → HCID 131714162, compound

Participants

Reaction Steps

A solution of Boc-Ser(tBu)-Asp(OtBu)-Ala-Val-Val-Asp(OtBu)-Thr(tBu)-Ser(tBu)-Ser(tBu)-Glu(OtBu)-OC6H5 (452 mg, 0.29 mmol) in TFE:H2O (5.2-0.4 mL) was treated with 3% H2O2 (0.31 mL, 0.30 mmol, 1.0 eq) with stirring (magnetic). The reaction mixture was adjusted to pH 10.5 by addition of 1N NaOH (triggered by an autotitrator) and maintained at that pH for 3 h. The reaction mixture was adjusted to pH ~1 with 1M HCl, refrigerated, filtered and washed with H2O and CH3OH and dried in vacuo. Yield: 423 mg (98.4%); mp ~245° dec; [α]D25 -13.28° (c 1, TFE); Rf 0.41 (CHCl3 :MeOH:AcOH; 80-2-0.4). Anal. calc. for C70H127N10O23.H2O (1494.87): C, 56.24; H, 8.69; N, 9.37. Found: C, 56.33; H, 8.32; N, 9.24.

Provenance & Evidence