Methanesulfonic Acid → (+)-1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine methanesulfonic acid salt

HRID 323246Notes

Reaction equation

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

Participants

Reactant 2

HCID 6395Methanesulfonic Acid

HCID 98097941-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

Product 1

HCID 22009167(+)-1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine methanesulfonic acid salt

Procedure

Prepare by the method of Example 3.7 using (−)-1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine (0.85 mmol) and methanesulfonic acid (0.32 g, 3.33 mmol) to give the title compound. [α]2D0=−1.6° (1.00, methanol).

Sources & evidence

ORD record: ord-6965b06d304d4086ad8c074ceddec213
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Reaction notes

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