1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → (S)-tert-butyl 2-(4-(((4-((E)-2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)vinyl)benzyl)(phenyl)amino)methyl)phenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 923449Notes

Reaction equation

HRID 923449 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]([CH2:14][C:15]2[CH:34]=[CH:33][C:18](/[CH:19]=[CH:20]/[C@@H:21]3[CH2:25][CH2:24][CH2:23][N:22]3[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:37]([O:41][C:42]([N:44]1[CH2:48][CH2:47][CH2:46][C@H:45]1[C:49](O)=[O:50])=[O:43])([CH3:40])([CH3:39])[CH3:38]>>[C:29]([O:28][C:26]([N:22]1[CH2:23][CH2:24][CH2:25][C@H:21]1/[CH:20]=[CH:19]/[C:18]1[CH:33]=[CH:34][C:15]([CH2:14][N:7]([CH2:6][C:5]2[CH:35]=[CH:36][C:2]([NH:1][C:49]([C@@H:45]3[CH2:46][CH2:47][CH2:48][N:44]3[C:42]([O:41][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:43])=[O:50])=[CH:3][CH:4]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:16][CH:17]=1)=[O:27])([CH3:31])([CH3:32])[CH3:30]

Participants

3

Reactant 2

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 59540411(S,E)-tert-butyl 2-(4-(((4-aminobenzyl)(phenyl)amino)methyl)styryl)pyrrolidine-1-carboxylate

Product 1

HCID 59540362(S)-tert-butyl 2-(4-(((4-((E)-2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)vinyl)benzyl)(phenyl)amino)methyl)phenylcarbamoyl)pyrrolidine-1-carboxylateYield 24.3%

Procedure

The product from Example 149F (700 mg, 1.45 mmol) and (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (374 mg, 1.74 mmol) were processed using the method described in Example 43 to afford 240 mg (23%) of the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 9.92 (s, 1H), 7.52 (d, J=8.4 Hz, 2H), 7.34 (d, J=7.9 Hz, 2H), 7.18 (m, 4H), 7.07 (m, 2H), 6.64 (d, J=8.1 Hz, 2H), 6.55 (t, J=7.7 Hz, 1H), 6.31 (d, J=15.6 Hz, 1H), 6.14 (dd, J=15.5, 6.5 Hz, 1H), 4.63 (s, 2H), 4.60 (s, 2H), 4.22 (m, 1H), 4.17 (m, 1H), 3.38 (m, 2H), 3.28 (m, 2H), 1.85 (m, 8H), 1.38 (s, 9H), 1.30 (s, 9H).

Sources & evidence

ORD record
ord-f1650e429c944fb6b1086b3126e0898a
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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