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CAS No. : | 57133-29-6 | MDL No. : | MFCD00151882 |
Formula : | C15H28N2O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RJOJSMIZZYHNQG-JTQLQIEISA-N |
M.W : | 332.39 | Pubchem ID : | 7015803 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
8% | Preparation of 15a, 15b, 15c: : (Boc)2-(L) Ornithine-OH (4.5 g, 13.6 mmols) (Bachem, Torrance, Calif.) was dissolved in 15 ml of DCM. To this was added 2.5 g (13.6 mmol) of pentafluorophenol. The reaction was cooled in an ice-bath followed by slow addition of 2.2 ml (13.6 mmols) of DIC. After complete addition the reaction mixture was stirred at room temperature for 30 minutes at which time the reaction mixture turned turbid (diisopropylcarbodimide-urea precipitation). To this mixture was then added 700 mg (1.43 mmols) of 2 followed by 1.6 g (13.6 mmol) of DMAP and the reaction was stirred at room temperature for 24 hours. The reaction mixture was transferred into a separatory funnel and washed with H2O (2×) 1% aq. HCl (2×), 0.1N aq. NaOH (2×), sat. NaHCO3 (3×), H2O (1×) and brine (1×), the organic layer was separated, dried over Na2SO4, filtered and the solvent was evaporated under vacuum. To the residue was then added 25 ml of diethylether and the urea was precipitated out. The filtrate was evaporated and the residue was purified using flash chromatography with solvent gradient of 2%-5% MeOH in DCM to furnish 690 mg (60%) of a mixture of products 15a, 15b, 15c, and 120 mg (8%) of the C3, C6 bis product.The 1HNMR showed major amounts of 15a and 15b products with 2% of the regioisomer 15c. 1HNMR of the mixture(15a, 15b and 15c): (CDCl3) delta ppm: 0.38 (1H, bs), 0.52 (1H, bs), 0.90-1.38 (m, 26H), 1.39-1.45 (s,m 27H), 1.59-1.63 (m, 5H), 1.76-1.82 (m, 2H), 1.96-2.01 (m, 4H), 2.16-2.20 (m, IH), 2.30-2.35 (d, 1H), 2.49-2.54 (q, 1H), 3.10-3.19 (m, 6H), 3.19-3.22 (m, 1H), 3.45-3.57 (t, 1H), 3.71-3.76 (m, 1H), 4.19-4.21 (m, 1H), 4.22-4.30 (m, 1H), 4.52-4.60 (m, 1H), 4.61-4.65 (m, 1H), 4.79-4.81 (m, 1H), 4.95-5.01 (m, 1H), 5.13-5.21 (m, 1H), 5.38-5.41 (m, 1H). MS (M+H) 804 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation of 15a, 15b, 15c: : (Boc)2-(L) Ornithine-OH (4.5 g, 13.6 mmols) (Bachem, Torrance, Calif.) was dissolved in 15 ml of DCM. To this was added 2.5 g (13.6 mmol) of pentafluorophenol. The reaction was cooled in an ice-bath followed by slow addition of 2.2 ml (13.6 mmols) of DIC. After complete addition the reaction mixture was stirred at room temperature for 30 minutes at which time the reaction mixture turned turbid (diisopropylcarbodimide-urea precipitation). To this mixture was then added 700 mg (1.43 mmols) of 2 followed by 1.6 g (13.6 mmol) of DMAP and the reaction was stirred at room temperature for 24 hours. The reaction mixture was transferred into a separatory funnel and washed with H2O (2×) 1% aq. HCl (2×), 0.1N aq. NaOH (2×), sat. NaHCO3 (3×), H2O (1×) and brine (1×), the organic layer was separated, dried over Na2SO4, filtered and the solvent was evaporated under vacuum. To the residue was then added 25 ml of diethylether and the urea was precipitated out. The filtrate was evaporated and the residue was purified using flash chromatography with solvent gradient of 2%-5% MeOH in DCM to furnish 690 mg (60%) of a mixture of products 15a, 15b, 15c, and 120 mg (8%) of the C3, C6 bis product.The 1HNMR showed major amounts of 15a and 15b products with 2% of the regioisomer 15c. 1HNMR of the mixture(15a, 15b and 15c): (CDCl3) delta ppm: 0.38 (1H, bs), 0.52 (1H, bs), 0.90-1.38 (m, 26H), 1.39-1.45 (s,m 27H), 1.59-1.63 (m, 5H), 1.76-1.82 (m, 2H), 1.96-2.01 (m, 4H), 2.16-2.20 (m, IH), 2.30-2.35 (d, 1H), 2.49-2.54 (q, 1H), 3.10-3.19 (m, 6H), 3.19-3.22 (m, 1H), 3.45-3.57 (t, 1H), 3.71-3.76 (m, 1H), 4.19-4.21 (m, 1H), 4.22-4.30 (m, 1H), 4.52-4.60 (m, 1H), 4.61-4.65 (m, 1H), 4.79-4.81 (m, 1H), 4.95-5.01 (m, 1H), 5.13-5.21 (m, 1H), 5.38-5.41 (m, 1H). MS (M+H) 804 Preparation of 16a, 16b, 16c To a 200 mg (0.25 mmol) of the mixture of 15a, 15b, 15c, was added 10 ml of 1.0M HCl/diethylether and strirred for 16 hrs. The white solids were filtered and washed with 10 ml of Et2O (4×). The solids were then dried under high vacuum for overnight to yield 160 mg (95%) of the target products 16a, 16b, 16c, as a white powder. The 1HNMR showed major amounts of 16a and 16b products with 2% of the C-16 (16c) regioisomer.1HNMR of the mixture (16a, 16b and 16c): (D2O) delta ppm: 0.26 (1H, bs), 0.52 (1H, bs), 0.90-1.18 (m, 26H), 1.49-1.74 (m, 5H), 1.83-2.10 (m, 2H), 2.20-2.31 (m, 4H), 2.81-2.92 (m, 2H), 3.19-3.20 (m, 1H), 3.39-3.42 (m, 1H), 3.62-3.71 (m, 1H), 3.88-4.00 (m, 1H), 4.08-4.12 (m, 1H), 4.52-4.57 (m, 1H), 4.61-4.65 (m, 1H), 4.79-4.81 (m, 1H). MS (M+H): 605. |
[ 57521-85-4 ]
(R)-2-((tert-Butoxycarbonyl)amino)pentanoic acid
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