* 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.
Reference：
[1] Synthetic Communications, 2004, vol. 34, # 20, p. 3751 - 3762
[2] Chemistry Letters, 2008, vol. 37, # 3, p. 320 - 321
[3] Tetrahedron Letters, 2003, vol. 44, # 21, p. 4007 - 4010
[4] Synthetic Communications, 1991, vol. 21, # 8-9, p. 981 - 987
[5] Bulletin de la Societe Chimique de France, 1965, p. 1308 - 1315
[6] Bulletin de la Societe Chimique de France, 1965, p. 1308 - 1315
[7] Canadian Journal of Chemistry, 1970, vol. 48, p. 1842 - 1849
[8] Journal of Medicinal Chemistry, 1977, vol. 20, # 8, p. 1059 - 1064
[9] Journal of Organic Chemistry, 1980, vol. 45, # 2, p. 348 - 349
[10] Journal of the American Chemical Society, 1967, vol. 89, p. 386 - 390
[11] Patent: US4014907, 1977, A,
2
[ 589-06-0 ]
[ 703-67-3 ]
Reference：
[1] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760
3
[ 589-06-0 ]
[ 3132-92-1 ]
Reference：
[1] Bulletin de la Societe Chimique de France, 1965, p. 1308 - 1315
[2] Journal of the American Chemical Society, 1967, vol. 89, p. 386 - 390
4
[ 366-77-8 ]
[ 589-06-0 ]
Yield
Reaction Conditions
Operation in experiment
35%
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 120 - 200℃; for 5 h; Dean-Stark
4-(4-Fluorophenyl)butanoic acid: 4-(4-Fluorophenyl)-4-oxobutanoic acid (0.98 g, 5 mmol) and KOH (85percent by wt, 0.79 g, 12 mmol) were placed in a round-bottomed flask fitted with a Dean-Stark apparatus and a reflux condenser and suspended in diethylene glycol (10 mL) at RT. Then, hydrazine monohydrate (50percent by wt., 1.20 g, 12 mmol) was added slowly to the reaction at RT after which it was heated to 120- 130 °C for 2 h. The reaction became homogenous after heating for approximately 45 min. After 2 h, the temperature was increased to 180-200 °C and the reaction stirred for an additional 3 h to remove residual hydrazine and water via the Dean-Stark trap. The reaction was then cooled to RT, diluted with H20 (10 mL), and poured into a 2.5 N aqueous solution of HQ (20 mL). The organic products were extracted with EtOAc (3 x 15 mL), washed with brine (10 mL), dried with anhydrous Na2S04, filtered, and concentrated in vacuo. Purification by column chromatography (30-50percent EtOAc/hexanes) afforded the desired product as a clear, viscous oil (0.32 g, 35percent). XH NMR (500 MHz, CDC13): δ 11.50 (br, 1H), 7.16 (m, 2H), 7.00 (m, 2H), 2.67 (t, J= 7.6 Hz, 2H), 2.40 (t, J= 7.4 Hz, 2H), 1.97 (quin, J= 7.5 Hz, 2H). 13C NMR (125 MHz, CDC13): δ 180.16, 161.34 (d, J= 243.4 Hz), 136.74, 129.76 (d, J= 7.3 Hz), 115.09 (d, J= 20.9 Hz), 34.09, 33.20, 26.24.
Reference：
[1] Patent: US5872118, 1999, A,
[2] Patent: US6124284, 2000, A,
[3] Patent: US5719186, 1998, A,
[4] Archiv der Pharmazie, 1998, vol. 331, # 12, p. 395 - 404
[5] Patent: WO2015/134973, 2015, A1, . Location in patent: Page/Page column 98
[6] Journal of the American Chemical Society, 1948, vol. 70, p. 3177
[7] Bulletin de la Societe Chimique de France, 1965, p. 1308 - 1315
[8] Journal of the American Chemical Society, 1967, vol. 89, p. 386 - 390
[9] Journal of Organic Chemistry, 1961, vol. 26, p. 2667 - 2669
[10] Patent: EP1403256, 2004, A1, . Location in patent: Page 8
[11] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5586 - 5590
[12] Angewandte Chemie - International Edition, 2016, vol. 55, # 51, p. 15797 - 15801[13] Angew. Chem., 2016, vol. 128, p. 16029 - 16033,5
5
[ 127404-66-4 ]
[ 589-06-0 ]
Reference：
[1] Synthetic Communications, 2004, vol. 34, # 20, p. 3751 - 3762
[2] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760
6
[ 366-77-8 ]
[ 589-06-0 ]
Reference：
[1] Patent: US2002/58659, 2002, A1,
7
[ 462-06-6 ]
[ 589-06-0 ]
Reference：
[1] Journal of the American Chemical Society, 1948, vol. 70, p. 3177
[2] Journal of Organic Chemistry, 1961, vol. 26, p. 2667 - 2669
[3] Bulletin de la Societe Chimique de France, 1965, p. 1308 - 1315
[4] Journal of the American Chemical Society, 1967, vol. 89, p. 386 - 390
8
[ 3200-99-5 ]
[ 589-06-0 ]
Reference：
[1] Bulletin de la Societe Chimique de France, 1965, p. 1308 - 1315
9
[ 582-83-2 ]
[ 589-06-0 ]
Reference：
[1] Bulletin de la Societe Chimique de France, 1965, p. 1308 - 1315
10
[ 459-57-4 ]
[ 589-06-0 ]
Reference：
[1] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760
b) Preparation of 4-(4-fluorophenyl)butyric acid A mixture of 3-(4-fluorobenzoyl)propanoic acid (42.3 g, 0.22 mol) and 10% Palladium on carbon (3 g) in acetic acid (250 mL) was hydrogenated at 50 psi and 25 C. for 6 h. The mixture was filtered and concentrated in vacuo. The residue was distilled at 0.02 mm Hg and the product crystallized to give 4-(4-fluorophenyl)butyric acid as a white solid (97%). m.p., 44-46.2 C. (lit. J. Am. Chem. Soc. 89, 386, 1967; m.p., 45.5-46.5 C.).
97%
palladium; In acetic acid;
b) Preparation of 4-(4-fluorophenyl)butyric acid A mixture of 3-(4-fluorobenzoyl)propanoic acid (42.3 g, 0.22 mol) and 10% Palladium on carbon (3 g) in acetic acid (250 mL) was hydrogenated at 50 psi and 25 C. for 6 h. The mixture was filtered and concentrated in vacuo. The residue was distilled at 0.02 mm Hg and the product crystallized to give 4-(4-fluorophenyl)butyric acid as a white solid (97%). m.p., 44-46.2 C. (lit. J. Am. Chem. Soc. 89, 386, 1967; m.p., 45.5-46.5 C.).
97%
palladium; In acetic acid;
b) Preparation of 4-(4-fluorophenyl)butyric acid A mixture of 3-(4-fluorobenzoyl)propanoic acid (42.3 g, 0.22 mol) and 10% Palladium on carbon (3 g) in acetic acid (250 mL) was hydrogenated at 50 psi and 25 C. for 6 h. The mixture was filtered and concentrated in vacuo. The residue was distilled at 0.02 mm Hg and the product crystallized to give 4-(4-fluorophenyl)butyric acid as a white solid (97%). m.p., 44-46.2 C. (lit. J. Chem. Soc. 89, 386, 1967; m.p., 45.5-46.5 C.).
35%
With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 120 - 200℃; for 5h;Dean-Stark;
4-(4-Fluorophenyl)butanoic acid: 4-(4-Fluorophenyl)-4-oxobutanoic acid (0.98 g, 5 mmol) and KOH (85% by wt, 0.79 g, 12 mmol) were placed in a round-bottomed flask fitted with a Dean-Stark apparatus and a reflux condenser and suspended in diethylene glycol (10 mL) at RT. Then, hydrazine monohydrate (50% by wt., 1.20 g, 12 mmol) was added slowly to the reaction at RT after which it was heated to 120- 130 C for 2 h. The reaction became homogenous after heating for approximately 45 min. After 2 h, the temperature was increased to 180-200 C and the reaction stirred for an additional 3 h to remove residual hydrazine and water via the Dean-Stark trap. The reaction was then cooled to RT, diluted with H20 (10 mL), and poured into a 2.5 N aqueous solution of HQ (20 mL). The organic products were extracted with EtOAc (3 x 15 mL), washed with brine (10 mL), dried with anhydrous Na2S04, filtered, and concentrated in vacuo. Purification by column chromatography (30-50% EtOAc/hexanes) afforded the desired product as a clear, viscous oil (0.32 g, 35%). XH NMR (500 MHz, CDC13): delta 11.50 (br, 1H), 7.16 (m, 2H), 7.00 (m, 2H), 2.67 (t, J= 7.6 Hz, 2H), 2.40 (t, J= 7.4 Hz, 2H), 1.97 (quin, J= 7.5 Hz, 2H). 13C NMR (125 MHz, CDC13): delta 180.16, 161.34 (d, J= 243.4 Hz), 136.74, 129.76 (d, J= 7.3 Hz), 115.09 (d, J= 20.9 Hz), 34.09, 33.20, 26.24.
With perchloric acid; hydrogen; acetic acid;palladium 10% on activated carbon;
Preparation 8 3-(4-Fluorobenzoyl)propionic acid (9.81g) was dissolved in acetic acid (50ml). 70% Perchloric acid (0.9ml) was added to the solution, and the mixture was hydrogenated with hydrogen (2 atmospheric pressure) in the presence of 10% palladium on carbon. The catalyst was removed by filtration with Celite, and the filtrate was distilled under vacuum. The resultant residue was dissolved in ethyl acetate, washed with water repeatedly and dried over magnesium sulfate. The solvent was removed under vacuum to give oily 4-(4-fluorophenyl)butyric acid (9.09g). This product was used in the subsequent reaction without further purification. Mass(APCI): m/z=182(M+), 181(M+-1);1H-NMR(CDCl3) delta : 1.94(2H, quintet, J=7.3Hz), 2.37(2H, t, J=7.3Hz), 2.65(2H, t, J=7.3Hz), 6.86-7.25(4H, m).
a. 7-Fluoro-1-tetralone A stirred mixture of 4-(p-fluorophenyl) butanoic acid (23g; 0.126 mole) and 85% polyphosphoric acid (200g) was heated at 100 C for 4 hrs., cooled, and poured onto ice-water (800g). After thorough stirring the precipitated tetralone was filtered off, washed well with water, and recrystallized from ethanol to give 13.07g (63%) of material of m.p. 56-57 C. (Found; C, 73.31; H, 5.72; C10 H9 FO requires; C, 73.13; H, 5.53%).
c) Preparation of 7-Fluoro-1-tetralone A mixture of <strong>[589-06-0]4-(4-fluorophenyl)butyric acid</strong> (68.2 g, 0.37 mol) and thionyl chloride (155 g, 1.3 mol) was refluxed for 1.25 h. The mixture was concentrated in vacuo to give 75.3 g (100%) of 4-(4-fluorophenyl)butyryl chloride)
75.3 g (100%)
With thionyl chloride;
c) Preparation of 7-Fluoro-1-tetralone A mixture of <strong>[589-06-0]4-(4-fluorophenyl)butyric acid</strong> (68.2 g, 0.37 mol) and thionyl chloride (155 g, 1.3 mol) was refluxed for 1.25 h. The mixture was concentrated in vacuo to give 75.3 g (100%) of 4-(4-fluorophenyl)butyryl chloride).
75.3 g (100%)
With thionyl chloride;
c) Preparation of 7-Fluoro-1-tetralone A mixture of <strong>[589-06-0]4-(4-fluorophenyl)butyric acid</strong> (68.2 g, 0.37 mol) and thionyl chloride (155 g, 1.3 mol) was refluxed for 1.25 h. The mixture was concentrated in vacuo to give 75.3 g (100%) of 4-(4-fluorophenyl)butyryl chloride)
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere;
General procedure: To an oven-dried 100 mL three-necked flask, 4-phenylbutyric acid (1.6 g, 10 mmol), DMF (5drops) and DCM (20 mL) were added under a N2 atmosphere. Oxalyl chloride (1.0 mL, 12 mmol,1.2 equiv.) was added dropwise at 0 C resulting in vigorous bubbling. The mixture was stirred for 3h at room temperature, and the solvent was then removed in vacuo. The resulting acid chloride wasused immediately without further purification. To a solution of acid chloride in DCM(30 mL), thesolution of 8-amino-5-chroloquinoline (2.1 g, 12 mmol, 1.2 equiv.), Et3N (2.5 mL, 24 mmol, 2equiv.) in DCM (15 mL) were added dropwise to the solution at 0 C, and the solution was thenwarmed to room temperature. After stirring overnight, the reaction system was quenched with sat. aq.NaHCO3 (30 mL) and the organic layer was separated. The aqueous layer was extracted with DCM(2 x 15 mL). The combined organic layers were washed with 1 M HCl aq. (30 mL) and brine (30mL), dried over MgSO4, filtered and evaporated in vacuo. The resulting crude amide was purified bycolumn chromatography on silica gel (eluant: hexane/EtOAc = 4/1) to afford the desired amide as awhite solid (2.5 g, 77%).
With phosphorus pentaoxide; phosphoric acid; at 10℃; for 1.5h;
Preparation 9 Polyphosphoric acid (newly prepared from phosphorous pentoxide (45g) and phosphoric acid (45ml)) was added to 4-(4-fluorophenyl) butyric acid (9.09g) with stirring at 10C. The mixture was stirred under the same condition for 1.5 hours. Ice-water was poured into the reaction mixture and extracted with ethyl acetate twice. The extracts were combined, washed with an aqueous solution of sodium bicarbonate, water and aqueous solution of sodium chloride and then dried over magnesium sulfate. The solvent was removed, and the resultant oily product (7.96g) was subjected to column chromatography on silica gel eluting with chloroform. Fractions containing the desired compound were combined and distilled under vacuum to give 7-fluoro-2-tetralone (4.75g) as colorless solid. Mass(APCI): m/z=165(M++1);1H-NMR(CDCl3) delta : 2.14(2H, quintet, J=6.4Hz), 2.66(2H, t, J=6.4Hz), 2.94(2H, t, J=6.4Hz), 7.12-7.28(3H, m), 7.69(1H, dd, J=2.7Hz, 9.2Hz).
Example 15 Synthesis of 1-[1-(4-fluorophenylbutyl) piperidin-4-yl]indoline 1-(Piperidin-4-yl)indoline (1.0 g) and <strong>[589-06-0]4-(4-fluorophenyl)butyric acid</strong> (0.9 g) were treated as in Example 8 to give the hydrochloride (0.23 g) of the title compound as a white powder (yield: 12%). m.p. (hydrochloride): 204-206 C. 1H-NMR (400 MHz, DMSO-d6): delta(ppm) 1.51-1.71(4H, m), 1.79-1.86(2H, m), 1.89-2.02(2H, m), 2.60(2H, t, J=7Hz), 2.87(2H, t, J=8Hz), 2.92-3.07(4H, m), 3.29(2H, t, J=7Hz), 3.47-3.53(2H, m), 3.62-3.72(1H, m), 6.48-6.56(2H, m), 6.92-7.02(2H, m), 7.06-7.12(2H, m), 7.20-7.28(2H, m), 9.99(1H, br-s). FAB-Mass: 353(MH+).
With triethylsilane; chloro-trimethyl-silane; sodium bicarbonate; triethylamine; In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;
Step 1 4-(4-Fluorophenyl)butyric Acid At 0 C., chlorotrimethylsilane (10.6 ml, 84.1 mmol) was added dropwise to a solution of 4-(4-fluorophenyl)-4-oxobutanoic acid (15.0 g, 76.5 mmol) and triethylamine (11.7 ml, 84.1 mmol) in THF (200 ml). The reaction mixture was stirred for 20 min at 0 C. The solid was filtered off. The solvent was removed from the solution. The residue was dissolved in DCM (200 ml). Triethylsilane (40 ml, 252 mmol) was added. An 1 N solution of titan(IV) chloride in DCM (229 ml, 229 mmol) was added dropwise while cooling with a water bath. The reaction mixture was stirred for 16 hours at room temperature. It was given onto ice water (300 ml). The phases were separated. The aqueous phase was extracted with DCM (100 ml). The combined organic phases were extracted with a saturated aqueous solution of sodium hydrogen carbonate (3*150 ml). The sodium hydrogen carbonate phases were combined and acidified with 1 N hydrochloric acid to pH 2. They were extracted with ethyl acetate (5*150 ml). The combined ethyl acetate layers were dried. The solvent was removed in vacuo to give 7.4 g of crude 4-(4-fluorophenyl)butyric acid, which was used in the next step without further purification. 1H NMR (DMSO-d6) delta1.80 (m, 2 H); 2.20 (t, 2 H); 2.60 (t, 2 H); 7.10 (m, 2H); 7.20 (m, 2 H); 12.05 (s, 1 H).
3-(4-fluorophenyl)propyl-1,1-dicarboxylic acid[ No CAS ]
[ 589-06-0 ]
Yield
Reaction Conditions
Operation in experiment
(3-2) 4-(4-Fluorophenyl)butyric acid The above 3-(4-fluorophenyl)propyl-1,1-dicarboxylic acid (6.938 g) was stirred at 180 C. for 40 min to give the title compound (4.877 g) as a brown oil. 1H-NMR (400 MHz, CDCl3): delta(ppm) 1.94(2H, m), 2.37(2H, t, J=7.6Hz), 2.65(2H, t, J=7.6Hz), 6.97(2H, t, J=8.8Hz), 7.15(2H, m).
1.1 Synthesis of t-butyl 4-(p-fluorophenyl)butyrate Scheme A, step 1: STR4 Combine <strong>[589-06-0]4-(p-fluorophenyl)butyric acid</strong> (51.4 g) and sulfuric acid (5.28 g, 98% Reagent ACS) in a Fisher-Porter bottle. Cool with a dry-ice bath to an internal temperature of between 0 C. and -20 C. Add isobutylene (54 g). Warm to ambient temperature. After 3 hours, cool in a dry-ice/acetone bath until the internal pressure differential of the vessel was 0 psi or less (about -20 C.). Carefully vent the Fisher-Porter bottle and add a cold solution of 5M sodium hydroxide (51.5 g). Reseal the Fisher-Porter bottle and allow to warm to ambient temperature with vigorous stirring. Vent the Fisher-Porter vessel to remove excess isobutylene. Extract the reaction mixture with toluene (75 g). Separate the organic layer and extract with a saturated sodium bicarbonate solution (77 g). Evaporate in vacuo to obtain the title compound. 1 H NMR (CDCl3, 300 MHz) delta 1.45 (s, 9H), 1.84 (m, 2H) 2.23 (t, J=7.5Hz, 2H), 2.61 (t, J=7.5 Hz, 2H), 6.96 (m, 2H), 7.13 (m, 2H).
With triethylamine; In tetrahydrofuran; 8-ethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole;
Reference Example 12 Preparation of 2-[beta-(p-fluorobenzoyl)propionyl]-8-ethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole To a solution of beta-(p-fluorobenzyl)propionic acid (3.0 g) and triethylamine (1.7 g) in dry tetrahydrofuran (90 ml) is added dropwise ethyl chloroformate (1.8 g) under maintaining the temperature of the system at 0 - 2C. The mixture is stirred at the same temperature for 30 minutes. The mixture is added in portions of 8-ethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (3.3 g) in dry tetrahydrofuran (50 ml) so that the temperature in the system is maintained at 0 - 2C. After the addition, the mixture is stirred at room temperature for one hour and then refluxed for one hour. After cooling, the precipitated crystals are filtered off and the filtrate is concentrated. The resulting residue is recrystallized from ethanol to give the titled compound (4.2 g), m.p. 120 - 124C.
General procedure: Various methyl-benzoates were commercially available and used without purification. Some methyl-benzoates (2 K, L, M, R and Q) were synthesized from benzoic acid. The benzoic acids were dissolved in anhydrous methanol and TMS-diazomethane solution 2.0 M in diethyl ether (4.0 equiv). The reactions were stirred at r.t for 1 h. The reactions were monitored by TLC. The reaction solvent was removed under reduced pressure. The products were purified by flash chromatography on silica gel with 10% ethyl acetate in hexane. The products were obtained as oiled solution. Yield 80-90%.
N-(9-fluorenylmethoxycarbonyl)-3-(β-naphthyl)-L-alanine[ No CAS ]
[ 204777-78-6 ]
[ 137076-54-1 ]
Fmoc-D-arginine[ No CAS ]
[ 204251-33-2 ]
C112H164FN25O27[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
9.7%
Stage #1: Fmoc-Lys(ivDde)-OH
Stage #2: With N-Acetylimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; 4-(4-fluorophenyl)butanoic acid; Fmoc-L-Lys(iPr,Boc)-OH; N-Fmoc L-Phe; Fmoc-Glu(OtBu)-OH; Fmoc-Tyr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-3-(β-naphthyl)-L-alanine; Fmoc-Lys(ivDde)-OH; 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane-10-acetic acid; Fmoc-D-arginine; γ-allyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate Further stages;
Synthesis of BL27
Fmoc-Rink Amide ProTide resin (CEM, 0.25 mmol, 0.58 mmol/g) was deprotected with 20% v/v piperidine in DMF for 1 min at 90°C twice. Fmoc-Lys(ivDde)-OH was then coupled to the resin. The resin was then capped using 1-acetylimidazole in DM F (0.1 w/v) at room temperature for 30 minutes. Fmoc-Lys(iPr,Boc)-OH, Fmoc-D-Glu(OAII)-OH, Fmoc-Gly-OH (coupled twice), Fmoc-2Nal-OH (coupled twice), Fmoc-D-Arg-OH (coupled twice for 4 mins each), Fmoc-Lys(iPr,Boc)-OH, Fmoc- Tyr(tBu)-OH, and Fmoc-Phe-OH (coupled twice) were sequentially coupled to the peptidyl resin. At a 0.1 mmol scale, the -OAllyl protecting group on D-Glu was removed using Pd(PPh3)4 (25 mg)/Phenylsilane (600 mL) in DCM (5 mL) (2 x 5 min at 35°C). The AT-Fmoc on Phe was then removed, and cyclization was performed using DIC/HOBt in DMF (3 c 10 min at 90°C). Following cyclization, the ivDde protecting group was removed by 2% v/v hydrazine in DMF (5 x 5 min at RT). From the synthesis of BL02, following the removal of the ivDde group, the resin (0.025 mmol) was coupled with Glu(OtBu), Lys(ivDde) and Glu(OtBu) sequentially. Afterwards, the chelator DOTA tri-f-butyl ester (4 equiv.) in DMF was coupled to the terminal amine with HATU/DIEA (4/8 equiv.) for 18 hours at room temperature. The ivDde protecting group was removed by 2% v/v hydrazine in DMF (5 x 5 min at RT). Fmoc-Gly-OH was then coupled. From the synthesis of BL19, following the coupling of Fmoc-Gly-OH, the Fmoc group was removed and 4-(4-fluorophenyl)butyric acid (4 equiv.) was coupled using HATU and DIEA (4 and 8 equiv.) for 10 minutes at 50 °C with two cycles. The peptide was deprotected and cleaved for 3.5 h at 35°C and the crude peptide mixture was worked up as previously described. The reaction mixture was purified by HPLC using the preparative column eluted with 20-40% acetonitrile in water with 0.1 % TFA over 15 mins at a flow rate of 30 mL/min. The retention time was 7.8 min, and the yield of the peptide was 9.7%.
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