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CAS No. : | 57159-62-3 | MDL No. : | MFCD01863457 |
Formula : | C9H11BrN2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WGMMKWFUXPMTRW-UHFFFAOYSA-N |
M.W : | 307.10 | Pubchem ID : | 4463814 |
Synonyms : |
N-Succinimidyl 3-(Bromoacetamido)propionate;3-(2-Bromoacetamido)propanoic acid NHS ester;WUN 59623
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisopropyl-carbodiimide; at 0 - 20℃; | [0078] N-BABA, compound 2, is reacted with N -hydroxysuccinimide (NHS) under conventional conditions well known in the art to generate SBAP, compound 3. Specially, N- BABA is combined with at least a stoichiometric amount of NHS in a suitable inert solvent such as methanol, ethanol, isopropanol and the like. The resulting solution is stirred at about 20 ± 5C until a clear solution is obtained. N-Diisopropylcarbodiimide is then added to the reaction mixture and mix with the generation of solids. The system is then cooled to 0 ± 5C and resulting SBAP is provided by filtration. Further purification entails prechilling a mixture of isopropanol and heptanes and washing the filter cakes followed by drying wet cake in a vacuum oven at about 30C. The resulting SBAP is used as is in the coupling reaction with the TT monomer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Succinimidyl 3-(bromoacetamido)propionate (SBAP). To a solution of β-bromoacetylβ-alanine (21.00 g, 100 mmol) and N-hydroxysuccinimide (13.01 g, 113 mmol) in 2-propanol (280 mL) at room temperature was added 1,3-diisopropyl-carbodiimide (16.0 mL, 101 mmol). After 8-10 min, oily precipitation of the product began, and the walls of the container were scratched to induce crystallization. The mixture was allowed to stand 1 h at room temperature and overnight at 4 C. The crystals were collected, washed with 2-propanol (30 mL), and redissolved in 2-propanol (200 mL brought to reflux). After an overnight stand at 4 C., the crystals were collected, washed with 2-propanol then hexane, and dried under vacuum/CaCl2. Yield, 22.9 g (74.6% of theory) mp 107-110.5 C. [lit. (23) 104-106 C.]; 1 H NMR (DMSO-d6) δ2.80 ppm (s, 4H, α"), 2.82 (t, 2H, α), 3.64 (q, 2H, β), 3.82 (s, 2H, α'), 7.03 (br, NH; 13 C NMR (CDCl3), δ25.62 (α"), 28.67 (α'), 31.39 (α), 35.65 (β), 166.20 (Ac C=O), 167.30,169.06 (C= O, s). Anal. Cald for C9 H11 BrN2 O5: C, 35.20; H, 3.61; N, 9.12; Br, 26.02. Found: C, 35.74; H 3.83; N, 9.20; Br, 26.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 1166 S-{2-[(3-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-3-oxopropyl)amino]-2-oxoethyl}-L-cysteine (5915) A suspension of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide (0.050 g, 0.099 mmol) and 4-methylmorpholine (0.054 ml, 0.493 mmol) in N,N-diisopropylethylamine (0.5 ml) was added to <strong>[57159-62-3]2,5-dioxopyrrolidin-1-yl 3-(2-bromoacetamido)propanoate</strong> (0.036 g, 0.118 mmol) in N,N-diisopropylethylamine (0.5 ml) and the mixture was stirred at room temperature. After 1 hour, (R)-2-amino-3-mercaptopropanoic acid (0.060 g, 0.493 mmol) as a solution in water (1 ml) was added. After 1 hour, a few drops of TFA were added to form a homogeneous solution and the mixture was purified by chromatography to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.28 (t, J=5.9 Hz, 1H), 8.85 (d, J=7.0 Hz, 1H), 8.47 (s, 2H), 8.30 (d, J=1.9 Hz, 1H), 8.21 (t, J=5.6 Hz, 1H), 8.17-8.09 (m, 2H), 7.84 (s, 1H), 7.81-7.74 (m, 2H), 7.44 (dd, J=7.0, 1.1 Hz, 1H), 7.27 (d, J=3.8 Hz, 1H), 4.65 (d, J=5.8 Hz, 2H), 4.20 (dd, J=7.5, 4.3 Hz, 1H), 4.06 (s, 2H), 3.90-3.78 (m, 2H), 3.35-2.94 (m, 8H), 2.59-2.41 (m, 2H), 1.57-1.19 (m, 4H), 0.95 (s, 3H); MS (ESI(+)) m/e 667 (M+H)+. |
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