H-HIS(BZL)-OH synthesis
- Product Name:H-HIS(BZL)-OH
- CAS Number:16832-24-9
- Molecular formula:C13H15N3O2
- Molecular Weight:245.28
20898-44-6
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$30.00/1g
16832-24-9
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$26.60/1G
Yield: 100%
Reaction Conditions:
with trifluoroacetic acid in dichloromethane at 20;Cooling with ice;Inert atmosphere;
Steps:
N-benzyl-L-histidine (12)
N-benzyl-L-histidine (12) Na-Boc-N(im)-benzyl-L-histidine 11 (Sigma-Aldrich) (750 mg, 2.17 mmol) was suspended in dichloromethane (10 mL), followed by the addition of trifluoroacetic acid (1 mL) with cooling in an ice bath. The resulting homogenous solution was allowed to stir at room temperatureuntil complete deprotection as showed by thin layer chromatography. Solvent was removed and triturated with Et20 (15 mL) and dried to afford the product 12 as white crystals (700 mg, quantitative). Mp: 230-233 °C, (Lit. 240 C)1; 1H NMR (400 MHz, DMSO) 69.01 (s, 1H, H-2’), 7.50 (s, 1 H, H-5’), 7.39 (m, 5H, Phenyl), 5.37 (s, 2H, H-i “), 4.22 (t, J = 7.0 Hz, 1 H, H-2), 3.22 (dd, J= 15.6, 7.0 Hz, 1H, H-3a), 3.14 (dd, J= 15.6, 7.0 Hz, 1H, H-3b); 130 NMR (101 MHz,DMSO) 6 170.1 (C-i), 136.3 (0-2’), 135.8 (C-2), 130.0 (0-4), 129.4 (0-5” C-6”), 129.0 (C-7’), 128.6 (C-3”C-4’), 120.6 (C-5’), 51 .7 (C-i ‘), 51 .6 (C-2), 26.3 (0-3) (Figs. 4 and 5).
References:
UNIVERSITY OF CAPE TOWN;JARDINE, Moegamat Anwar;KHONDE, Lutete Peguy WO2016/46618, 2016, A1 Location in patent:Page/Page column 21
100-44-7
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71-00-1
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16832-24-9
59 suppliers
$26.60/1G
57101-60-7
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