Hexane → 5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide p-toluenesulfonate

HRID 1873548Notes

Reaction equation

HRID 1873548 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([NH:14][CH2:15][C:16]([N:18]3[CH2:22][C@@H:21]([F:23])[CH2:20][C@H:19]3[C:24]#[N:25])=[O:17])([CH3:13])[CH2:12][CH:7]2[CH2:6]1)=[O:4].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.CCCCCC>ClCCl.CC(C)=O>[C:28]1([CH3:38])[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:35])=[O:36])=[CH:32][CH:33]=1.[CH3:26][N:2]([CH3:1])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([NH:14][CH2:15][C:16]([N:18]3[CH2:22][C@@H:21]([F:23])[CH2:20][C@H:19]3[C:24]#[N:25])=[O:17])([CH3:13])[CH2:12][CH:7]2[CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 8058HexaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 687768935-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-N,N,5-trimethyl-hexahydro-cyclopenta[c]pyrrole-2(1H)-carboxamide

Product 1

HCID 866483435-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide p-toluenesulfonateYield 97.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

5-[2-(2-Cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 18a (0.9 g, 2.47 mmol) was dissolved in 5 mL of dichloromethane with stirring at room temperature. To a solution of p-toluenesulfonic acid monohydrate (469 mg, 2.47 mmol) in 3 mL of acetone was added the above mentioned solution, which resulted in the formation of a white precipitate. The reaction mixture was stirred for 30 minutes followed by addition of 1 mL of n-hexane. The mixture was filtered to obtain the title compound 5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide p-toluenesulfonate 18 (1.3 g, yield 93%) as a white solid.

Workup

  1. customresulted in the formation of a white precipitate
  2. stirringThe reaction mixture was stirred for 30 minutes
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-12802d7ca0fe4a759a9533beeec56297
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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