Hydrochloric Acid → HCID 101039217, compound

Participants

Reaction Steps

To a stirred solution of H—NMeAib—Phe—OMe, HCl salt (0.3 g, 1.0 mmol) in CH2Cl2 (3mL) was added TEA (0.28 mL, 2.0 mmol). After stirring for 5 min at room temperature p-nitrobenzoyl chloride (0.15 g, 1 mmol) was added. The resulting solution was stirred at room temperature for 24 h. The solvent was removed in vacuo and redissolved in ethyl acetate (30 mL). The ethyl acetate layer was washed with 1M HCl (3×10 mL) brine (10 mL), 10% aq. Na2CO3 (3×10 mL), brine (10 mL), and dried over Na2SO4. Evaporation of the solvent was followed by column chromatography of the product with CHCl3—MeOH-Acetic Acid (90:10:0.1 v:v:v) provided 7a (see Table 1) (100 mg 24%) as a pale yellow amorphous solid: mp.65-70° C.; 1H NMR (360 MHz CDCl3 δ) 1.54 &1.52 (2s, 6H, β-MeAib), 2.87 (s, 3H, N—CH3), 3.15 (d, 2H, J=5.04 Hz, β-H), 3.69 (s, 3H, O—CH3), 4.86 (m, 1H, α-H); 6.35 (d, 1H, J=6.35 Hz, N—H), 7.20 (m, 5H, Aromatic Phe), 7.55 (d, 2H, J=8.64 Hz, Benzyl-H), 8.64 (d, 2H, J=8.64 Hz, Benzyl-H), FAB-MS m/z (relative intensity) 428 (35%), 450 (40%), 249 (100%); [α]D20−16.15° (c 0.014, MeOH).

Provenance & Evidence