BOC-11-AMINOUNDECANOIC ACID

White powder

160 g of 11-aminoundecanoic acid, 2 liters of dioxane, 1.3 liters of distilled water, 208 g of sodium carbonate and 173 g of di-tert-butyl dicarbonate are successively introduced into a 4-liter three-necked flask equipped with a mechanical stirrer and a reflux condenser. Preparation of intermediate 24f2To a solution of 24f1 (1.0g, 4.97mmol) in MeOH (40ml), TEA (1 .04ml, 7.45mmol) was added, followed by di t-butyl dicarbonate (2.17g, 9.94mmol). The reaction was heated at 60oC for 1 .5hr. The reaction was concentrated and purified over Si02 column with 5percent MeOH/DCM to afford 1 .2g compound 24f2 (80percent yield). General procedure: To a mixture of NaOH (43 mg, 1.1 mmol), in water/tert-BuOH 1:1 (1.0 mL) was added di-tert-butyl dicarbonate (225 μL, 1.05 mmol) and 12-amino-dodecan-1-ol (199 mg, 1.00 mmol). After the viscous mixture was stirred for 18 h, 0.3 M HCl solution (1.5 mL) was added and the aqueous layer was extracted with ethyl acetate (3 .x. 30 mL). The combined organic layers were washed with brine (5 mL) and dried over MgSOSodium hydroxide (2.18 g, 54.5 mmol) was added to a suspension of 11-aminoundecanoic acid (1) (5.00 g, 24.8 mmol) in a mixture of tetrahydrofuran and water (260 mL, 1:1). The resulting solution was stirred for 10 minutes, then di-tert-butyl dicarbonate (6.50 g, 29.8 mmol) added and the reaction stirred at ambient temperature for 14 hours. The solvent was then removed under vacuum. The resulting white solid was dissolved in chloroform, and the solution washed with a 1 N HC1 (3 x 100 mL), dried over anhydrous magnesium sulfate and concentrated to give 3 (6.99 g, 93percent) as a white solid: *H NMR (500 MHz, CDC1Into a flask were added 11-aminoundecanoic acid (12a, 1.00 g, 4.97 mmol, 1 equiv) and dioxane (6.2 mL, 0.8 M). Sodium hydroxide (0.19 g, 5.0 mmol, 1 equiv) was dissolved in water (10 mL, 0.8 M) and added to the dioxane solution. The mixture was cooled in an ice bath (0 °C, 20 min). Di-tert-butyl dicarbonate (1.19 g, 5.46 mmol, 1.1 equiv) was dissolved in dioxane (6.2 mL) and added. The suspension was stirred vigorously and allowed to gradually warm to ambient temperature (26 h). Volatiles were removed under reduced pressure. The residue was dissolved in a mixture of water (40 mL) and saturated sodium bicarbonate (10 mL), washed with EtOAc (2 x 30 mL), acidified with sodium bisulfate (1 M, 30 mL, to pH 2), extracted with EtOAc (40 mL plus 2 x 30 mL), and dried with sodium sulfate. Volatiles were removed under reduced pressure to yield pure carbamate 12b (1.16 g, 3.85 mmol, 79percent yield), which was used directly in the next step. Compound analysis is consistent with published data. The synthesis, unblocking, and purification of peptide (2) were conducted using the same method as that for the peptide in Example 1. To protect the Nomega-function of arginine, the nitro group from the omega-amino group of lysine, the chorocarbobenzoxy group, was used. To synthesize the peptide, 0.2 g of N-tert-butyloxycarbonyl-Nomega-nitroarginine methylbenzhydryl amino polymer and 10 ml of dimethylformamide were added to a reaction vessel. The content of the arginine derivative was 1.0 mmol/g of the polymer. (0025) Upon completion of the polypeptide chain assembly, the final unblocking of the protected peptidyl-polymer with simultaneous cleavage of the peptide from the polymer with liquid hydrogen fluoride were conducted. Purification was conducted with an acetonitrile gradient of 10-90% in 0.1% trifluoroacetic acid. According to the optical density data, the content of the main substance, peptide NH2-(CH2)10-CO-Ile-Leu-Pro-D-Phe-Lys-D-Phe-Pro-D-Phe-D-Phe-Pro-D-Phe-Arg-Arg-NH2 was at least 99%. The amino acid composition of the peptide and its molecular weight corresponded to the theoretical values.

Molecular Weight:301.42
XLogP3:4.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:13
Exact Mass:301.22530847
Monoisotopic Mass:301.22530847
Topological Polar Surface Area:75.6
Heavy Atom Count:21
Complexity:297
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes