Trifluoroacetic acid → HCID 131712844, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.0 g (3.2 mmoles) H-Pro-Ser-NH2.CF3COOH (2) in 35 ml dimethylformamide is cooled at 0° C., then 0.36 ml (3.2 mmoles) N-methyl-morpholine are added, followed by 1.2 g (3.2 mmoles) Boc-Tyr (Bzl)-OH, 0.43 g (3.2 mmoles) 1-hydroxybenzotriazole, and 0.73 g (3.52 mmoles) dicyclohexylcarbodiimide. The reaction mixture is stirred for 1 hour at 0° C. and at room temperature overnight, then it is filtered, and evaporated in vacuo. The residue is dissolved in ethyl acetate and the solution washed successively with NaCl-saturated solutions of 1 M citric acid, 1 M NaHCO3, and water. The organic solution is dried over anhydrous Na2SO4 and the solvent removed in vacuo. The (3) product is recovered by crystallization from ethyl acetate-petroleum ether: 1.4 g, m.p. 115° C.; [α]D25 -22.9° (c=1, MeOH); RfA =0.20

Provenance & Evidence