N-[(Phenylmethoxy)carbonyl]-L-isoleucine → {(r)-3-[(s)-2-((s)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-methyl-butyrylamino]-2-hydroxy-propyl}-cyclohexylmethyl-phosphinic acid benzyl ester

Participants

Reaction Steps

The title compound was prepared substantially in a similar manner as Step 1, Example 10 using N-Z-Ile-OH and [(R)-3-((S)-2-amino-3-methyl-butyrylamino)-2-hydroxy-propyl]-cyclohexylmethyl-phosphinic acid benzyl ester hydrochloride as the starting materials. The title compound was purified by SiO2 chromatography using 0-4% MeOH/CH2Cl2 as the eluent. 1H NMR (CD3OD, 300 MHz): δ 7.3 (m, 10H), 5.2-4.95 (m, 4H), 4.17 (d, 1H), 4.12 (m, 1H), 3.95 (d, 1H), 3.20 (m, 2H), 2.12-2.01 (m, 1H), 1.90-1.76 (m, 3H), 1.70-1.61 (m, 6H), 1.55-1.47 (m, 3H), 1.36-1.14 (m, 4H), 1.11-0.95 (m, 14H). 31P NMR (CD3OD, 300 MHz): δ 59.06, 58.33. LCMS m/z: [M+H]+=672.

Provenance & Evidence