1h and 13c nmr of ledipasvir - hepatitis c · 2017-04-29 · sf01 = 125.77 mhz sw = 250.55 ppm d1 =...
TRANSCRIPT
1H AND 13C NMR OF LEDIPASVIR
ORGANISATION: NATIONAL MEASUREMENT INSTITUTE
Page 2/19
LEDISPAVIR
F FN
NH
N
O
NH
O
O
H
N
HN
N
O
NH
O
O 1H NMR in DMSO-d6
SF01 = 500.13 MHz SW = 12.0016 Hz D1 = 40 seconds NS = 64 scans
10 9 8 7 6 5 4 3 2 1 0 ppm
0.492
0.511
0.521
0.529
0.545
0.851
0.864
0.876
0.922
0.936
0.962
0.975
2.496
2.500
2.504
3.349
3.541
3.548
3.702
3.721
3.809
3.829
5.179
5.189
5.195
5.205
7.223
7.240
7.319
7.336
7.517
7.958
8.070
3.6
1
1.1
6
13.4
2
0.1
0
1.1
0
1.3
6
2.5
7
4.3
7
5.7
0
0.3
1
1.0
8
1.2
1
1.2
0
28.4
7
6.0
7
2.3
4
2.5
1
1.1
5
1.2
3
1.0
5
0.2
7
0.1
1
0.2
8
0.6
8
2.0
0
2.5
3
9.1
5
Page 3/19
6.26.36.46.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.4 ppm
6.384
6.462
6.774
6.792
6.811
6.829
6.922
6.939
7.223
7.240
7.319
7.336
7.500
7.517
7.528
7.545
7.599
7.616
7.702
8.070
0.2
8
0.6
8
2.0
0
2.5
3
9.1
5
4.44.54.64.74.84.95.05.15.25.35.4 ppm
4.548
4.630
4.653
4.667
4.830
4.874
5.148
5.163
5.179
5.189
5.195
5.205
5.335
5.347
5.409
5.421
1.1
5
1.2
3
1.0
5
0.2
7
0.1
1
Page 4/19
3.13.23.33.43.53.63.73.83.94.04.14.2 ppm
3.082
3.186
3.204
3.418
3.541
3.548
3.702
3.721
3.767
3.809
3.829
3.943
3.960
3.980
3.996
4.013
4.065
4.079
4.093
4.112
4.143
4.159
4.175
28.4
7
6.0
7
2.3
4
2.5
1
1.51.61.71.81.92.02.12.22.32.42.52.62.7 ppm
1.452
1.471
1.542
1.564
1.599
1.718
1.742
1.766
1.784
1.791
1.798
1.814
1.890
1.912
1.928
1.955
1.963
1.976
1.986
2.001
2.023
2.033
2.048
2.058
2.083
2.192
2.208
2.217
2.233
2.395
2.413
2.500
2.657
1.1
0
1.3
6
2.5
7
4.3
7
5.7
0
0.3
1
1.0
8
1.2
1
1.2
0
Page 5/19
1.0 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 ppm0.511
0.521
0.529
0.545
0.558
0.566
0.577
0.583
0.591
0.609
0.620
0.628
0.681
0.689
0.699
0.708
0.718
0.795
0.809
0.823
0.851
0.864
0.876
0.922
0.936
0.962
0.975
3.6
1
1.1
6
13.4
2
Page 6/19
13C NMR in DMSO-d6
SF01 = 125.77 MHz SW = 250.55 ppm D1 = 2 seconds NS = 8192 scans
2030405060708090100110120130140150160170180190200210220230240 ppm
9.43
10.82
35.49
39.18
39.35
39.52
39.69
39.85
42.54
60.70
60.75
109.37
111.67
132.59
133.19
133.89
134.57
138.20
138.22
143.10
169.88
170.42
206.54
145150155160165170175 ppm
141.68
141.84
143.10
143.82
149.36
149.37
155.32
155.43
156.86
156.89
169.88
170.22
170.42
Page 7/19
105110115120125130135 ppm
109.37
111.67
113.58
113.61
116.71
118.97
119.24
120.40
121.05
121.29
121.34
121.80
121.85
123.32
125.24
127.90
131.13
131.22
132.59
133.19
133.89
134.57
135.79
136.17
136.24
137.31
137.36
137.50
137.54
137.66
138.20
138.22
525354555657585960616263646566676869 ppm
51.46
51.49
54.34
54.91
57.77
57.79
58.01
60.70
60.75
Page 8/19
202530354045 ppm
17.66
18.20
18.46
18.54
19.07
19.27
19.30
21.11
27.08
29.73
30.05
30.70
30.94
35.49
42.54
Page 9/19
COSY in DMSO-d6
SF01 = 500.133 MHz SW = 12.016 ppm NS = 4 scans
ppm
11 10 9 8 7 6 5 4 3 2 1 0 ppm
11
10
9
8
7
6
5
4
3
2
1
0
Page 10/19
HSQC in DMSO-d6
13C SF01 = 125.77 MHz SW = 165.64 ppm
1H SF01 = 500.13 MHz SW = 13.36 ppm NS = 4 scans
ppm
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
20
40
60
80
100
120
140
160
180
200
220
240
Page 11/19
HMBC in DMSO-d6
13C SF01 = 125.77 MHz SW = 12.0160 ppm
13C SF01 = 500.13 MHz SW = 6685 ppm NS = 8 scans
ppm
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
20
40
60
80
100
120
140
160
180
200
220
240
Page 12/19
1H NMR in MeOH-d4
SF01 = 500.13 MHz SW = 14.9960 Hz D1 = 5 seconds NS = 8 scans
-112 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.909
0.929
0.943
0.962
1.001
1.017
1.030
2.147
2.498
3.236
3.310
3.653
3.673
4.887
5.266
5.281
5.296
7.331
7.797
7.826
7.851
7.866
7.898
7.944
8.034
19.7
0
14.3
1
1.9
1
1.3
1
0.9
6
5.9
6
1.1
2
1.0
0
1.2
9
1.0
2
1.0
7
1.2
8
1.3
4
12.4
1
7.17.27.37.47.57.67.77.87.98.08.18.28.38.4 ppm
7.331
7.383
7.417
7.460
7.511
7.525
7.546
7.558
7.591
7.607
7.619
7.636
7.654
7.697
7.710
7.721
7.736
7.760
7.797
7.826
7.851
7.866
7.944
8.034
12.4
1
Page 13/19
4.604.654.704.754.804.854.904.955.005.055.105.155.205.255.305.355.405.45 ppm
4.606
4.817
4.887
5.266
5.281
5.296
5.430
5.444
1.0
7
1.2
8
1.3
4
3.13.23.33.43.53.63.73.83.94.04.14.24.34.4 ppm
3.307
3.310
3.313
3.503
3.653
3.673
3.718
3.784
3.800
3.818
3.921
3.940
4.112
4.127
4.151
4.166
4.358
4.371
0.9
6
5.9
6
1.1
2
1.0
0
1.2
9
1.0
2
Page 14/19
1.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.9 ppm
1.596
1.616
1.635
1.648
1.669
1.766
1.783
1.835
1.856
1.877
1.891
1.899
1.906
1.922
1.936
1.959
1.988
2.005
2.018
2.032
2.196
2.326
2.345
2.498
2.812
14.3
1
1.9
1
1.3
1
1.1 1.0 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 ppm
0.608
0.617
0.626
0.655
0.664
0.674
0.691
0.697
0.713
0.722
0.730
0.773
0.781
0.792
0.800
0.845
0.865
0.878
0.909
0.929
0.943
0.962
1.001
1.017
1.030
19.7
0
Page 15/19
13C NMR in MeOH-d4
SF01 = 125.77 MHz SW = 250.55 ppm D1 = 2 seconds NS = 8192 scans
20406080100120140160180200220240 ppm
17.98
18.01
18.28
18.53
30.67
46.47
52.74
63.86
120.89
121.82
123.06
123.15
124.41
129.70
132.15
139.66
139.86
143.47
156.01
158.43
159.40
172.70
173.24
173.34
210.05
120125130135140145150155160165170175 ppm
120.89
121.82
123.06
123.15
124.41
129.70
132.15
139.66
139.86
143.47
156.01
158.43
159.40
172.70
173.24
173.34
Page 16/19
525354555657585960616263646566676869 ppm
52.50
52.74
56.25
56.95
58.18
58.23
59.39
59.58
59.68
59.87
60.17
63.02
63.86
202530354045 ppm
17.98
18.01
18.28
18.53
19.56
19.83
19.93
20.16
22.62
27.83
28.34
30.67
31.04
31.59
31.84
31.88
32.32
33.21
34.30
37.15
40.77
43.90
46.47
Page 17/19
COSY in MeOH-d4
SF01 = 500.133 MHz SW = 12.016 ppm NS = 4 scans
ppm
11 10 9 8 7 6 5 4 3 2 1 0 ppm
11
10
9
8
7
6
5
4
3
2
1
0
Page 18/19
HSQC in MeOH-d4
13C SF01 = 125.77 MHz SW = 250 ppm
1H SF01 = 500.13 MHz SW = 13.3654 ppm NS = 4 scans
ppm
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
20
40
60
80
100
120
140
160
180
200
220
240
Page 19/19
HMBC in MeOH-d4
13C SF01 = 125.77 MHz SW = 221.8327 ppm
1H SF01 = 500.13 MHz SW = 12.0160 ppm NS = 8 scans
ppm
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
20
40
60
80
100
120
140
160
180
200
220
240