FMoc-Val-Cit-PAB-PNP synthesis
- Product Name:FMoc-Val-Cit-PAB-PNP
- CAS Number:863971-53-3
- Molecular formula:C40H42N6O10
- Molecular Weight:766.8
5070-13-3
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159858-22-7
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863971-53-3
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$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
7693-46-1
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$18.00/5g
159858-22-7
197 suppliers
$14.00/25MG
863971-53-3
188 suppliers
$16.00/1mg
67-56-1
738 suppliers
$7.29/5ml-f
5070-13-3
232 suppliers
$5.00/5g
159858-22-7
197 suppliers
$14.00/25MG
863971-53-3
188 suppliers
$16.00/1mg
130878-68-1
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863971-53-3
188 suppliers
$16.00/1mg
68858-20-8
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$8.00/1g
863971-53-3
188 suppliers
$16.00/1mg