N-[(Phenylmethoxy)carbonyl]-L-histidine → {(R)-3-[(S)-2-Amino-3-(lH-imidazol-4-yl)-propionylamino]-2-hydroxy-propyl}-cyclohexylmethyl-phosphinic acid

Participants

Reaction Steps

The title compound was prepared substantially following the procedures as set forth in Step 4, Example 1, Method A, and employing ((R)-3-Amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride and N-Cbz-L-histidine-OH as the starting materials. Subsequent hydrogenation of the resulting product in accordance with the procedures of Step 5, Example 1, Method B, and RP-HPLC purification yielded the title compound. 1H NMR (CD3OD, 300 MHz): δ 8.16 (s, 1H), 7.19 (s, 1H), 4.15 (t, 1H), 4.12-3.98 (m, 1H), 3.38-3.10 (m, 4H), 1.94 (br.d, 2H), 1.85-1.60 (m, 6H), 1.56 (dd, 2H), 1.40-1.16 (m, 3H), 1.15-0.96 (m, 2H). 31P NMR (CD3OD, 300 MHz): δ 41.59. LCMS m/z: [M+H]+=373.2

Provenance & Evidence