L-Leucine → (2S)-N-[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]-4-methylpentanamide hydrochloride

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Reaction Steps

The procedure described for 5c was used. Deprotection of 75 mg of 5a and coupling with 72 mg of (2S)-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]-4-methylpentanoic acid (prepared from L-leucine and 4-methoxy-2,3,6-trimethylphenylsulfonylchloride using the procedure described for 5b) yielded after purification the title compound (65 mg) as a mixture of diastereomers (1:1). 1H-NMR 400 MHz (CD3OD) δ: 0.50 and 0.68 (3H, 2x d, J=7 Hz), 0.61 and 0.79 (3H, 2x d, J=7 Hz), 0.97-1.65 (9H, m), 2.13 (3H, s), 2.54 and 2.56 (3H, 2x s), 2.61 and 2.62 (3H, 2x s), 2.76-3.68 (7H, m), 3.78 and 3.84 (3H, 2x s), 4.98-5.02 and 5.18-5.22 (1H, 2x m), 6.71 (1H, s), 7.16-7.19 (1H, m), 7.53-7.78 (4H, in), 8.29-8.34 (1H, m).

Provenance & Evidence