Hydroxybenzenesulfonic acid → HCID 46854533, compound

HRID 1099388Notes

Reaction equation

HRID 1099388 reaction equation
[CH2:1]([O:3][C:4]([C:6]12[CH2:13][CH2:12][C:9]([NH:14][CH2:15][C:16]([N:18]3[CH2:22][C@@H:21]([F:23])[CH2:20][C@H:19]3[C:24]([NH2:26])=[O:25])=[O:17])([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)=[O:5])[CH3:2].O.[C:28]1([S:34]([OH:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl.ClCCl.CO>[C:28]1([S:34]([OH:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH2:1]([O:3][C:4]([C:6]12[CH2:13][CH2:12][C:9]([NH:14][CH2:15][C:16]([N:18]3[CH2:22][C@@H:21]([F:23])[CH2:20][C@H:19]3[C:24]([NH2:26])=[O:25])=[O:17])([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 15619088Hydroxybenzenesulfonic acidHCID 46854534(2S,4S)-1-[2-[(4-ethoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carboxamide

Product 1

HCID 46854533HCID 46854533, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

(2S,4S)-1-[2-[(4-Ethoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carboxamide (1.00 g) was dissolved in dichloromethane (10 mL), and a suspension of benzenesulfonic acid monohydrate (500 mg) in dichloromethane-methanol (5:1, 6 mL) was added thereto, followed by stirring at room temperature for 3 hours. The precipitate were collected by filtration, washed with dichloromethane (5 mL) and then dried, thereby obtaining a colorless solid of (2S,4S)-1-[2-[(4-ethoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carboxamide benzenesulfonate (1.15 g, yield: 81%).

Workup

  1. additionwas added
  2. filtrationThe precipitate were collected by filtration
  3. washwashed with dichloromethane (5 mL)
  4. customdried

Sources & evidence

ORD record
ord-ce408b5cadae4ae489ed6b2f07aba731
Source dataset
uspto-grants-2012_03
Patent number
US08143427B2

Reaction notes

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