p-Toluenesulfonic acid monohydrate → HCID 86612240, compound

HRID 2246791Notes

Reaction equation

HRID 2246791 reaction equation
[C:1]([C:3]1([NH:6][C:7](=[O:40])[C@H:8]([CH2:35][C:36]([F:39])([CH3:38])[CH3:37])[NH:9][C@@H:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C@H:26]4[CH2:28][C@@H:27]4[C:29]([NH:31][CH:32]4[CH2:34][CH2:33]4)=[O:30])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH:11]([F:13])[F:12])[CH2:5][CH2:4]1)#[N:2].[CH3:41][C:42]1[CH:43]=[CH:44][C:45]([S:48]([OH:51])(=[O:50])=[O:49])=[CH:46][CH:47]=1.O>C1COCC1>[CH3:41][C:42]1[CH:43]=[CH:44][C:45]([S:48]([O-:51])(=[O:50])=[O:49])=[CH:46][CH:47]=1.[C:1]([C:3]1([NH:6][C:7](=[O:40])[C@@H:8]([NH2+:9][C@@H:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C@@H:26]4[CH2:28][C@H:27]4[C:29]([NH:31][CH:32]4[CH2:34][CH2:33]4)=[O:30])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH:11]([F:12])[F:13])[CH2:35][C:36]([F:39])([CH3:38])[CH3:37])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58869058HCID 58869058, compound

Product 1

HCID 86612240HCID 86612240, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N1-(1-cyanocyclopropyl)-N2-[(1S)-1-(4′-{(1S,2S)-2-[(cyclopropylamino)carbonyl]cyclopropyl}biphenyl-4-yl)-2,2-difluoroethyl]-4-fluoro-L-leucinamide (60 mg, 0.11 mmol) was dissolved in 0.80 mL of THF. TsOH.H2O (21 mg, 0.11 mmol) was dissolved in 0.20 mL of THF and was added to the reaction mixture. It was stirred at room temperature for 30 minutes. Hexanes (∫3 mL) was then added until a precipitate crashed out of solution. It was sonicated for 5 minutes and it was filtered off on a Buchner funnel. The white solid was dried on the pump overnight. It was triturated in diethyl ether (˜5 mL) for 2 h at room temperature and filtered off on a Buchner funnel to yield the title compound.

Workup

  1. additionwas added to the reaction mixture
  2. customIt was sonicated for 5 minutes
  3. filtrationit was filtered off on a Buchner funnel
  4. customThe white solid was dried on the pump overnight
  5. customIt was triturated in diethyl ether (˜5 mL) for 2 h at room temperature
  6. filtrationfiltered off on a Buchner funnel

Sources & evidence

ORD record
ord-9440603db8d444a58f62887c06d9dcb7
Source dataset
uspto-grants-2010_03
Patent number
US07687524B2

Reaction notes

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