1-Pentanaminium, 5-carboxy-5-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-N,N,N-trimethyl-, chloride (1:1), (5S)-

White to off-white powder

N-Trimethyl lysine 1. A solution of Fmoc-N-£-(trimethyl)-L-lysine hydrochloride (0.032 g), 2-(3H-[ I , 2, 3 ]triazolo[ 4, S-b ]pyridin-3-yl)-I, I , 3, 3-tetramethylisouronium hexafluorophosphate(V) (0.028 g)and N, N-diisopropylethylamine (0.034 mL) in N, N-dimethylformamide (O.S mL) was stirred for Sminutes. The reaction was added to Example 1.13.7 (O.OSO g), and stirring was continued at room10 temperature overnight. Diethylamine (0.069 mL) was added to the reaction, and stirring wascontinued for an additional2 hours. The reaction was diluted with N, N-dimethylformamide (1 mL), water (O.S mL), and trifluoroacetic acid (0.10I mL). The mixture was purified by reverse phaseHPLC using a Gilson system, eluting with 10-90% acetonitrile in water containing O.I% v/vtrifluoroacetic acid. The desired fractions were combined and freeze-dried to provide the title15 compound. 1H NMR (SOO MHz, dimethyl sulfoxide-d6) 8 ppm I2.87 (s, IH), 8.13 (s, 3H), 8.04 (d, IH), 7.80 (d, IH), 7.62 (d, IH), 7.S4-7.42 (m, 3H), 7.42-7.34 (m, 2H), 7.29 (s, IH), 6.96 (d, IH), 4.96(s, 2H), 4.42-4.24 (m, IH), 3.89 (t, 2H), 3.82 (s, 2H), 3.29-3.I6 (m, 2H), 3.08-3.00 (m, ISH), 2.87 (s, 2H), 2.10 (s, 3H), 1.84-1.60 (m, 4H), 1.42-0.97 (m, ISH), 0.8S (s, 6H). MS (ESI) m/e 930.3 (M+Ht.[000628] A solution of Fmoc-N-8-(trimethyl)-L-lysine hydrochloride (0.032 g), 2-(3H- [l, 2, 3]triazolo[4, 5-b]pyridin-3-yl)-l, l, 3, 3-tetramethylisouronium hexafluorophosphate(V) (0.028 g) and N, N-diisopropylethylamine (0.034 mL) in N, N-dimethylformamide (0.5 mL) was stirred for 5 minutes. The reaction was added to Example 1.13.7 (0.050 g), and stirring was continued at room temperature overnight. Diethylamine (0.069 mL) was added to the reaction, and stirring was continued for an additional 2 hours. The reaction was diluted with Nu, Nu-dimethylformamide (1 mL), water (0.5 mL), and trifluoroacetic acid (0.101 mL). The mixture was purified by reverse phase HPLC using a Gilson system, eluting with 10-90% acetonitrile in water containing 0.1% v/v trifluoroacetic acid. The desired fractions were combined and freeze-dried to provide the title compound. Ti NMR (500 MHz, dimethyl sulfoxide-t/g) delta ppm 12.87 (s, 1H), 8.13 (s, 3H), 8.04 (d, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.54-7.42 (m, 3H), 7.42-7.34 (m, 2H), 7.29 (s, 1H), 6.96 (d, 1H), 4.96 (s, 2H), 4.42-4.24 (m, 1H), 3.89 (t, 2H), 3.82 (s, 2H), 3.29-3.16 (m, 2H), 3.08-3.00 (m, 15H), 2.87 (s, 2H), 2.10 (s, 3H), 1.84-1.60 (m, 4H), 1.42-0.97 (m, 15H), 0.85 (s, 6H). MS (ESI) m/e 930.3 (M+H)+.A solution of Fmoc-N-epsilon-(trimethyl)-L-lysine hydrochloride (0.032 g), 2-(3H- [1, 2, 3]triazolo[4, 5-b]pyridin-3-yl)-1, 1, 3, 3-tetramethylisouronium hexafluorophosphate(V) (0.028 g) and N, N-diisopropylethylamine (0.034 mL) in N, N-dimethylformamide (0.5 mL) was stirred for 5 minutes. The reaction was added to Example 1.13.7 (0.050 g), and stirring was continued at room temperature overnight. Diethylamine (0.069 mL) was added to the reaction, and stirring was continued for an additional 2 hours. The reaction was diluted with N, N-dimethylformamide (1 mL), water (0.5 mL), and trifluoroacetic acid (0.101 mL). The mixture was purified by reverse phase HPLC using a Gilson system, eluting with 10-90% acetonitrile in water containing 0.1% v/v trifluoroacetic acid. The desired fractions were combined and freeze-dried to provide the title compound. 1H NMR (500 MHz, dimethyl sulfoxide-d6) delta ppm 12.87 (s, 1H), 8.13 (s, 3H), 8.04 (d, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.54-7.42 (m, 3H), 7.42-7.34 (m, 2H), 7.29 (s, 1H), 6.96 (d, 1H), 4.96 (s, 2H), 4.42-4.24 (m, 1H), 3.89 (t, 2H), 3.82 (s, 2H), 3.29-3.16 (m, 2H), 3.08-3.00 (m, 15H), 2.87 (s, 2H), 2.10 (s, 3H), 1.84-1.60 (m, 4H), 1.42-0.97 (m, 15H), 0.85 (s, 6H). MS (ESI) m/e 930.3 (M+H)+.

Molecular Weight:447.0
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:10
Exact Mass:446.1972352
Monoisotopic Mass:446.1972352
Topological Polar Surface Area:75.6
Heavy Atom Count:31
Complexity:566
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes