p-Toluenesulfonic acid monohydrate → HCID 86641015, compound

HRID 1099390Notes

Reaction equation

HRID 1099390 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([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>CC(O)C>[C:28]1([CH3:38])[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:35])=[O:36])=[CH:32][CH:33]=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

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 46854534(2S,4S)-1-[2-[(4-ethoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carboxamide

Product 1

HCID 86641015HCID 86641015, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

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 2-propanol (10 mL) with heating, and a solution of 4-toluenesulfonic acid monohydrate (541 mg) in 2-propanol (4 mL) was added thereto. After ice-cooling and subsequent 1 hour of stirring, the precipitate were collected by filtration, washed with 2-propanol (5 mL) and then blast-dried at 60° C., thereby obtaining a colorless solid of (2S,4S)-1-[2-[(4-ethoxycarbonylbicyclo[2.2.2]-oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carboxamide 4-toluenesulfonate (1.28 g, yield: 88%).

Workup

  1. temperaturewith heating
  2. temperatureAfter ice-cooling and subsequent 1 hour
  3. filtrationthe precipitate were collected by filtration
  4. washwashed with 2-propanol (5 mL)
  5. customblast-dried at 60° C.

Sources & evidence

ORD record
ord-d62921fec3434a79a4a5c3312e4d321c
Source dataset
uspto-grants-2012_03
Patent number
US08143427B2

Reaction notes

Loading…