(R)-2-phenyl-2-(piperidin-1-yl)acetic acid → (S)-tert-butyl 2-(4-(((4-fluorophenyl)(4-((S)-1-((R)-2-phenyl-2-(piperidin-1-yl)acetyl)pyrrolidine-2-carboxamido)benzyl)amino)methyl)phenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 923420Notes

Reaction equation

HRID 923420 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]([C@@H:34]3[CH2:38][CH2:37][CH2:36][N:35]3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:33])=[CH:27][CH:26]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C@@H:19]3[CH2:23][CH2:22][CH2:21][NH:20]3)=[O:18])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[C:46]1([C@@H:52]([N:56]2[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]2)[C:53](O)=[O:54])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]([C@@H:34]3[CH2:38][CH2:37][CH2:36][N:35]3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:33])=[CH:27][CH:26]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C@@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:53](=[O:54])[C@@H:52]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:56]3[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61]3)=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1090523(R)-2-phenyl-2-(piperidin-1-yl)acetic acidHCID 59540402(s)-Tert-butyl 2-(4-(((4-fluorophenyl)(4-((s)-pyrrolidine-2-carboxamido)benzyl)amino)methyl)phenylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 59540361(S)-tert-butyl 2-(4-(((4-fluorophenyl)(4-((S)-1-((R)-2-phenyl-2-(piperidin-1-yl)acetyl)pyrrolidine-2-carboxamido)benzyl)amino)methyl)phenylcarbamoyl)pyrrolidine-1-carboxylateYield 58.3%

Procedure

The product from Example 114A (0.26 g, 0.42 mmol) and (R)-2-phenyl-2-(piperidin-1-yl)acetic acid (0.12 g, 0.55 mmol) was processed as in Example 81A to give 0.20 g (58%) of the title compound as a white solid.

Sources & evidence

ORD record
ord-9fd8dccc2435418d9b453138d9316158
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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