Structural Elucidation of Hybutimibe

doi:10.11938/cjmr20233065

Abstract

Abstract:

The structure of hybutimibe was analyzed by ultraviolet absorption spectroscopy, infrared absorption spectroscopy, mass spectrometry, nuclear magnetic resonance (¹H NMR, ¹³C NMR, DEPT, ¹H-¹H COSY, ¹H-¹H NOESY, ¹H-¹³C HSQC and ¹H-¹³C HMBC) spectroscopy and single crystal diffraction. The ¹H and ¹³C NMR signals of hybutimibe were assigned. The crystal structure of hybutimibe was studied by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and powder X-ray diffraction (PXRD).

Key words: hybutimibe, nuclear magnetic resonance (NMR), mass spectrometry, infrared absorption spectroscopy, structural elucidation

CLC Number:

O482.53

XU Xiaojie, CHEN Yan’an, LI Xufei, ZHANG Yuncai, ZHANG Yong, ZHAN Dongkai, PAN Ting. Structural Elucidation of Hybutimibe[J]. Chinese Journal of Magnetic Resonance, 2024, 41(1): 43-55.

Figures/Tables 15

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Table 1

Table 2

References 9

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Assignment	δ_C	DEPT	HMBC	δ_H	δ_H(DMSO-d₆)	COSY	NOESY(DMSO-d₆)
4	26.9	CH₂	3.25(H2),4.73(H3), 5.84(H5)	2.85(m,2H)	2.75(m,2H)	3.25(H2), 5.84(H5)	3.20(H2), 4.36(H7), 4.90(H3), 5.77(H5)
7	59.6	CH₂	5.84(H5)	4.50,4.58 (d,J=12.4 Hz,2H)	4.36 (d,J=5.3 Hz,2H) 4.84 (OH,t,J=5.3 Hz,1H)	/	2.75(H4), 7.38(H9,H13)
2	59.9	CH	4.73(H3),5.84(H5)	3.25(m,1H)	3.20(m,1H)	2.85(H4), 4.73(H3)	2.75(H4)
3	60.3	CH	2.85(H4),3.25(H2), 7.18(H15,H19)	4.73(d,J=2.0 Hz,1H)	4.90 (d,J=2.4 Hz,1H)	3.25(H2)	2.75(H4), 7.19(H15,H19)
10,12	115.3(d,J=22 Hz)	CH	6.98(H10,H12), 7.38(H9,H13)	6.98(t,J=8.7 Hz,2H)	7.12 (m,2H)	7.38(H9,H13)	/
22,24	115.9(d,J=23 Hz)	CH	6.92(H22,H24)	6.92(t,J=8.6 Hz,2H)	7.12(m,2H)	7.26(H21,H25)	/
16,18	116.2	CH	6.84(H16,H18)	6.84(d,J=8.4 Hz,2H)	6.70 (d,J=8.6 Hz,1H)	7.18(H15,H19)	/
21,25	118.7(d,J=8Hz)	CH	7.26(H21,H25)	7.26(dd,J=4.6/8.9 Hz,2H)	7.19(m,2H)	6.92(H22,H24)	/
5	126.1	CH	2.85(H4),3.25(H2), 4.50(H7),4.58(H7)	5.84(t,J=8.1 Hz,1H)	5.77 (t,J=7.7 Hz,1H)	2.85(H4)	7.38(H9,H13)
15,19	127.4	CH	4.73(H3), 7.18(H15,H19)	7.18(d,J=8.4 Hz,2H)	7.19(m,2H)	6.84(H16,H18)	4.90(H3)
9,13	128.1(d,J=8Hz)	CH	7.38(H9,H13)	7.38(dd,J=5.5, 8.5 Hz,2H)	7.38(m,2H)	6.98(H10,H12)	4.36(H7), 5.77(H5)
14	128.8	C	3.25(H2), 6.84(H16,H18)	/	/	/	/
20	133.6(d,J=2Hz)	C	6.92(H22,H24), 7.26(H21,H25)	/	/	/	/
8	137.0 ( d,J=4Hz)	C	4.50(H7),4.58(H7), 5.84(H5), 6.98(H10,H12)	/	/	/	/
6	141.2	C	2.85(H4),4.50(H7), 4.58(H7),5.84(H5), 7.38(H10,H12)	/	/	/	/
17	156.3	C	6.84(H16,H18), 7.18(H15,H19)	/	9.48(OH,s,1H)	/	6.70(H16,H18)
23	159.2 (d,J=243Hz)	C	6.92(H22,H24), 7.26(H21,H25)	/	/	/	/
11	162.3(d,J=245Hz)	C	6.98(H10,H12), 7.38(H9,H13)	/	/	/	/
1	167.8	C	2.85(H4),3.25(H2), 4.73(H3)	/	/	/	/

Assignment	δ_C		δ_H
Assignment	hybutimibe	ezetimibe	hybutimibe	ezetimibe
4	26.9(CH₂)	24.50(CH₂)	2.85(m, 2H)	1.73, 1.83
7	59.6(CH₂)	/	4.50, 4.58(d, J=12.4 Hz, 2H)
2	59.9(CH)	59.40(CH)	3.25(m, 1H)	3.09
3	60.3(CH)	59.58(CH)	4.73(d, J =2.0 Hz, 1H)	4.81
10,12	115.3(CH, 22)	114.64(CH, 21.0)	6.98(t, J =8.7 Hz, 2H)	7.11
22,24	115.9(CH, 23)	115.79(CH, 22.5)	6.92(t, J=8.6 Hz, 2H)	7.13
16,18	116.2(CH)	115.71(CH)	6.84(d, J=8.4 Hz, 2H)	6.76
21,25	118.7(CH, 8)	118.22(CH, 8.0)	7.26(dd, J=4.6/8.9 Hz, 2H)	7.22
5	126.1(CH)	36.36(CH₂)	5.84(t, J=8.1 Hz, 1H)	1.73
15,19	127.4(CH)	127.52(CH)	7.18(d, J=8.4 Hz, 2H)	7.18
9,13	128.1(CH, 8)	127.50(CH, 9.0)	7.38(dd, J=5.5/8.5 Hz, 2H)	7.32
14	128.8(C)	127.88(C)	/
20	133.6(C, 2)	133.98(C, 2.3)	/
8	137.0(C, 4)	142.19(C, 2.9)	/
6	141.2(C)	71.05(CH)	/	4.50
17	156.3(C)	157.42(C)	/	1.73, 1.83
23	159.2(C, 243)	157.05, 158.96(C, 240.2)	/
11	162.3(C, 245)	160.06, 161.98(C, 241.5)	/	3.09
1	167.8(C)	167.33(C)	/	4.81

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