Spectroscopic Studies of Delafloxacin Meglumine

doi:10.11938/cjmr20202855

Abstract

Abstract:

The structure of delafloxacin meglumine was analyzed by infrared absorption (IR), ultraviolet absorption (UV), nuclear magnetic resonance (¹H NMR, ¹³C NMR, DEPT, ¹H-¹H COSY, ¹H-¹³C HSQC and ¹H-¹³C HMBC) spectroscopy, mass spectrometry and elemental analysis. The characteristic absorption peaks in the IR spectra were discussed. The ¹H and ¹³C NMR signals of delafloxacin meglumine were assigned, and the two-dimensional signals were used to elucidate its structure. The crystal structure of delafloxacin meglumine was studied by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and powder X-ray diffraction (PXRD).

Key words: delafloxacin meglumine, nuclear magnetic resonance (NMR), infrared absorption spectroscopy, structural elucidation, crystal structure

CLC Number:

O482.53

Xin-yi ZHAO,Dong HAN,Hong-jun LUO,Wen-bin SHEN,Gong-jun YANG. Spectroscopic Studies of Delafloxacin Meglumine[J]. Chinese Journal of Magnetic Resonance, 2021, 38(2): 268-276.

Figures/Tables 9

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Table 1

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Table 2

References 9

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吸收峰波数/cm^-¹	振动类型	基团
3484, 3311, 3183	O-H伸缩振动	醇（-OH）
	N-H伸缩振动	伯胺（Ar-NH₂）
3080	=C-H伸缩振动	=C-H
2992, 2937, 2872	C-H伸缩振动	烷基
2872	-NH₂⁺对称、不对称伸缩振动	铵盐（R₁R₂NH₂⁺）
1631, 1586, 1552	C=O伸缩振动	共轭酮羰基
	C=N、C=C伸缩振动	烯键、吡啶环
1631	N-H弯曲振动	伯胺（Ar-NH₂），铵盐（R₁R₂NH₂⁺）
1586, 1491	苯环骨架C=C伸缩振动	苯环
1586, 1395	-CO₂^-对称、不对称伸缩振动	羧酸盐（ArCOO^-）
1458, 1425	C-H弯曲振动	亚甲基，环丁基
1425	O-H弯曲振动	醇（-OH）
1395	C-H弯曲振动	N-甲基
1325	C-N伸缩振动	伯胺（Ar-NH₂）
1228	C-F伸缩振动	氟代杂芳环（Ar-F）
1172, 1076	C-O伸缩振动	醇（-OH）
1110	C-Cl伸缩振动	氯代苯（Ar-Cl）
821	=C-H面外弯曲振动	取代芳环

Position	δ_C(J/Hz)	δ_H (J/Hz)	¹H -¹H COSY	HMBC
2	148.3	8.36 (1H, s)	/	/
3	115.2	/	/	H-2
4	174.1 (d, ⁴J_CF=1.4 Hz)	/	/	H-2, H-5
5	110.2 (d, ²J_CF =22.6 Hz)	7.76 (1H, d, ³J_HF =14.0 Hz)	/	/
6	149.9 (d, ¹J_CF =246.8 Hz)	/	/	H-5
7	141.6 (d, ²J_CF =11.8 Hz)	/	/	H-5, H-17, H-18
8	118.7 (d, ³J_CF =6.7 Hz)	/	/	H-2, H-5
9	135.7	/	/	H-2, H-5
10	104.9 (d, ³J_CF =5.4 Hz)	/	/	H-2, H-5
11	134.4 (dd, J=4.2/13.1 Hz)	/	/	H-5, H-13, NH₂
12	142.7 (dd, J=4.5/242.0 Hz)	/	/	H-13
13	113.6 (t, ²J_CF =22.3 Hz)	7.88 (1H, t, ³J_HF=9.4 Hz)	/	/
14	144.7 (dd, J=5.2/253.1 Hz)	/	/	H-13, NH₂
15	145.6 (d, ²J_CF =14.3 Hz)	/	/	H-13
16	166.9	/	/	H-2
17	66.5 (d, ⁴J_CF =4.5 Hz)	4.64 (2H, m)	H-18	/
		4.12 (2H, m)
18	61.2 (d, ⁵J_CF =4.5 Hz)	4.46 (1H, quint, J=6.2 Hz)	H-17	H-17
19	63.5	3.61 (1H, dd, J=3.3/10.9 Hz)	H-20	H-20, H-21
		3.42 (1H, dd, J=5.6/10.9 Hz)
20	71.3	3.52 (1H, m)	H-19, H-21	H-19, H-21, H-22
21	70.7	3.47 (1H, dd, J=1.0/8.0 Hz)	H-20, H-22	H-19, H-20, H-23
22	70.3	3.69 (1H, d, J=4.0 Hz)	H-21, H-23	H-20, H-23, H-24
23	69.4	3.89 (1H, quint, J=3.5 Hz)	H-22, H-24	H-21, H-22, H-24
24	52.0	2.94 (1H, dd, J=3.4/12.4 Hz)	H-23	H-22, H-23, H-25
		2.85 (1H, dd, J=7.9/12.4 Hz)
25	34.1	2.49 (3H, s)	/	H-24
NH₂	/	6.64 (2H, s, br)	/	/

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