N-(Methoxycarbonyl)-L-tert-leucine → N-(methoxycarbonyl)-3-methyl-L-valyl-N-(4-{[{4-[(E)-2-{(2S)-1-[N-(methoxycarbonyl)-3-methyl-L-valyl]pyrrolidin-2-yl}ethenyl]benzyl}(phenyl)amino]methyl}phenyl)-L-prolinamide

HRID 923451Notes

Reaction equation

HRID 923451 reaction equation
[C:1]1([N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([C@@H:32]3[CH2:36][CH2:35][CH2:34][NH:33]3)=[O:31])=[CH:25][CH:24]=2)[CH2:8][C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C@@H:17]3[CH2:21][CH2:20][CH2:19][NH:18]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:37][O:38][C:39]([NH:41][C@@H:42]([C:46]([CH3:49])([CH3:48])[CH3:47])[C:43](O)=[O:44])=[O:40]>>[CH3:37][O:38][C:39]([NH:41][C@H:42]([C:43]([N:33]1[CH2:34][CH2:35][CH2:36][C@H:32]1[C:30]([NH:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12](/[CH:15]=[CH:16]/[C@@H:17]3[CH2:21][CH2:20][CH2:19][N:18]3[C:43](=[O:44])[C@H:42]([C:46]([CH3:49])([CH3:48])[CH3:47])[NH:41][C:39]([O:38][CH3:37])=[O:40])=[CH:13][CH:14]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:28][CH:27]=1)=[O:31])=[O:44])[C:46]([CH3:47])([CH3:48])[CH3:49])=[O:40]

Participants

3

Reactant 2

HCID 11263950N-(Methoxycarbonyl)-L-tert-leucineHCID 66749838(S)-N-(4-((phenyl(4-((E)-2-((S)-pyrrolidin-2-yl)vinyl)benzyl)amino)methyl)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 59540267N-(methoxycarbonyl)-3-methyl-L-valyl-N-(4-{[{4-[(E)-2-{(2S)-1-[N-(methoxycarbonyl)-3-methyl-L-valyl]pyrrolidin-2-yl}ethenyl]benzyl}(phenyl)amino]methyl}phenyl)-L-prolinamideYield 55%

Procedure

The product from Example 149H (35 mg, 0.73 mmol) and (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid (33.1 mg, 0.175 mmol) were processed using the method described in Example 43 to afford 33 mg (55%) of the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 9.98 (s, 1H), 7.50 (d, J=8.4 Hz, 2H), 7.28 (d, J=8.3 Hz, 2H), 7.17 (m, 4H), 7.06 (m, 3H), 6.63 (m, 2H), 6.55 (t, J=7.3 Hz, 1H), 6.37 (d, J=15.7 Hz, 1H), 6.22 (m, 1H), 6.17 (dd, J=16.0, 6.3 Hz, 1H), 4.63 (m, 1H), 4.61 (s, 2H), 4.58 (s, 2H), 4.42 (m, 1H), 4.19 (m, 2H), 3.77 (m, 1H), 3.70 (m, 1H), 3.63 (m, 2H), 3.52 (s, 6H), 2.16 (m, 2H), 1.96 (m, 2H), 1.84 (m, 4H), 0.95 (s, 9H), 0.93 (s, 9H).

Sources & evidence

ORD record
ord-095921921fa8412cba2e7caaf758920e
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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