ChemicalBook CAS DataBase List FMoc-Val-Cit-PAB-PNP

FMoc-Val-Cit-PAB-PNP synthesis

8synthesis methods

Product Name:FMoc-Val-Cit-PAB-PNP
CAS Number:863971-53-3
Molecular formula:C40H42N6O10
Molecular Weight:766.8

5070-13-3 Synthesis

5070-13-3
249 suppliers
$5.00/5g

159858-22-7 Synthesis

159858-22-7
208 suppliers
$14.00/25MG

863971-53-3
203 suppliers
$16.00/1mg

Yield:863971-53-3 89%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide at 20; for 1 h;Inert atmosphere;

Steps:

a
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N⁵-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide (1.3 g, 2.16 mmol) (prepared as reported in EP0624377A2) and bis(4-nitrophenyl) carbonate (1.32 g, 4.34 mmol) were dissolved in 6 mL of dry DMF under nitrogen atmosphere, DIPEA (0.75 mL, 4.35 mmol) was added and the resulting solution was stirred an hour at room temperature. Diethylether (120 mL) was added, the resulting precipitate is filtered off, washed with diethylether and dried under vacuum affording N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N⁵- carbamoyl-N-[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide (1.47 g, 89% yield).ESI MS: m/z 767 (MH+)¹H NMR (400 MHz, DMSO-de) δ 0.86 (d, J = 6.7 Hz, 3 H), 0.88 (d, J = 6.7 Hz, 3 H), 1.30 - 1.52 (m, 2 H), 1.60 (m, 1 H), 1.69 (m, 1 H), 1.99 (m, 1 H), 2.90 - 3.10 (m, 2 H), 3.93 (dd, J = 8.9, 7.0 Hz, 1 H), 4.14 - 4.34 (m, 3 H), 4.42 (m, 1 H), 5.24 (s, 2 H), 5.39 (s, 2 H), 5.97 (t, J = 5.5 Hz, 1 H), 7.32 (m, 2 H), 7.42 (m, 5 H), 7.55 (m, 2 H), 7.65 (d, J = 8.4 Hz, 2 H), 7.74 (t, J = 7.9 Hz, 2 H), 7.88 (d, J = 7.6 Hz, 2 H), 8.12 (d, J = 7.4 Hz, 1 H), 8.31 (m, 2 H), 10.12 (s, 1 H)

References:

NERVIANO MEDICAL SCIENCES S.R.L.;CALDARELLI, Marina;CARUSO, Michele;ORSINI, Paolo WO2015/44003, 2015, A1 Location in patent:Page/Page column 39

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7693-46-1 Synthesis