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Nα-Fmoc-Lys(Nε-Boc)-OHWang resin-Val-Asp(Allyl)-Tyr(O-t-Bu)-NH2[ No CAS ]
(S)-2-[(2S,5S,8S,11S,14S,21S)-5-(4-Amino-butyl)-21-((S)-2-amino-3-methyl-butyrylamino)-11-benzyl-2-(4-hydroxy-benzyl)-8-(1H-indol-3-ylmethyl)-3,6,9,12,19,22-hexaoxo-1,4,7,10,13,18-hexaaza-cyclodocosane-14-carbonyl]-amino}-succinic acid[ No CAS ]
3-(3-allyloxycarbonylamino-propyl)-4-oxo-2-<i>p</i>-tolylcarbamoyl-1,2,3,4,6,7,12,12b-octahydro-pyrazino[1',2':1,2]pyrido[3,4-<i>b</i>]indole-6-carboxylic acid[ No CAS ]
(3S,6S,12bS)-2-Allylcarbamoyl-3-(3-allyloxycarbonylamino-propyl)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-pyrazino[1',2':1,2]pyrido[3,4-b]indole-6-carboxylic acid[ No CAS ]
With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;
General procedure: Compound 5 (35.2 g, 0.135 mol) was added to a three-necked flask.Acetone (300 mL), water (300 mL),Sodium bicarbonate (22.7 g, 0.27 mol) and Fmoc-OSu (45.5 g, 0.135 mol) were then added.The reaction solution was stirred at room temperature for 12 hours.Petroleum ether extraction (500 mL3);The aqueous phase was acidified to pH 3 with 1N hydrochloric acid and extracted with ethyl acetate (500 mL EtOAc).The organic phases were combined and washed with saturated brine (500 mL).Dry over sodium sulfate and filter. Evaporate some of the ethyl acetate,Adding petroleum ether crystalline compound 6(N-fluorenylmethoxycarbonyl-N'-tert-butoxycarbonyl-homolysine)(57.3 g, yield 88%, HPLC purity:98.1%, ee: 99%).
C. SYNTHESIS OF FMOC-ORN(ALOC)-OH. This amino acid derivative was prepared in the manner described above for lysine. Orn(AlOC)-OH . Ornithine hydrochloride [60 g; 0.375 moles] was dissolved in 800 mL of water and 9 g of NaOH was added. CuSO4 [47 g; 0.1875 moles] was added to this solution, whereupon the mixture became deep blue in color; it was stirred until all solids had dissolved. Next, 100 g of NaHCO3 was added, followed by allyl chloroformate [56.8 g; 0.4125 moles) in 300 mL of dioxane. The mixture bubbled and was stirred overnight. A sky blue solid was collected on a paper filter, and suspended in 2 L of hot water. H2S was bubbled through for 3 hours, and the black suspension was filtered and allowed to stand for 24 hours. The resulting yellow solution was concentrated to 500 mL and chilled overnight. White crystals were obtained and collected and washed with cold water. The mother liquor was further concentrated, yielding a second crop of crystals. Both batches appeared identical by TLC analysis (solvent system of ethyl acetate: pyridine: water: acetic acid, 35:20:11:6, vol/vol). The yield was 41.9 g (51.5% from Orn-HCl), mp 260C (decomposed). The product was analyzed by NMR and compositional analysis; results are shown below. 1H NMR (200 MHz, D 2 O) ppm : 6.0 - 5.7 (m) 1 H; 5.3 - 5.0 (m) 2 H; 4.5 - 4.4, (d) J = 5 Hz, 2 H; 3.7 - 3.5 (t) J = 7 Hz, 1 H; 3.2 - 3.0 (t) J = 6 Hz, 2 H; 1.9 - 1.6 (m) 2 H; 1.6 - 1.3 (m) 2 H. Analysis calculated for C8H16N2O4: C, 49.99. H, 7.45. N, 12.95. Analysis found: C, 50.09. H, 7.56. N, 13.14.
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