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

HRID 323244Notes

Reaction equation

HRID 323244 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:37]=[C:38]([O:42][CH3:43])[C:39]=1[O:40][CH3:41])[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[NH:32][C:31]4[CH:33]=[CH:34][CH:35]=[CH:36][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].[CH3:44][S:45]([OH:48])(=[O:47])=[O:46]>C(OCC)(=O)C>[CH3:44][S:45]([OH:48])(=[O:47])=[O:46].[CH3:43][O:42][C:38]1[CH:37]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:39]=1[O:40][CH3:41])[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[NH:29][C:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=4[N:32]=3)[CH2:23][CH2:22]2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9]1)=[O:7]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 99382691-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

Product 1

HCID 22009082(+)-1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt) (0.95 g, 1.62 mmol) and ethyl acetate (75 mL). Add a solution of methanesulfonic acid (0.80 g, 8.33 mmol) in ethyl acetate (4 mL). After 18 hours, decant the solvent. Add diethyl ether and stir. After 1 hour, decant, add diethyl ether and stir. After another hour, decant, collect the solid. Combine the solid and methanol and evaporate in vacuo to give a solid. dry in vacuo at 82° C. to give the title compound: mp; 91-104° C. [α]2D0=+1.3° (0.98, methanol).

Workup

  1. customdecant the solvent
  2. waitAfter 1 hour
  3. customdecant
  4. additionadd diethyl ether
  5. stirringstir
  6. waitAfter another hour
  7. customdecant
  8. customcollect the solid
  9. customevaporate in vacuo
  10. customto give a solid
  11. customdry in vacuo at 82° C.

Sources & evidence

ORD record
ord-f9da69889f684d63bcaf4de867e5ed68
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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