Toluene → HCID 86667793, compound

HRID 389905Notes

Reaction equation

HRID 389905 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20](=[O:21])[C@@:19]([CH2:28][O:29][C:30](=[O:43])[C@@H:31]([NH:35]C(OC(C)(C)C)=O)[CH:32]([CH3:34])[CH3:33])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:18]([CH3:44])[C:17]2=[O:45])=[CH:12][C:11]=1[C:46]([F:49])([F:48])[F:47])#[N:9].C1(C)C=CC=CC=1.[Cl:57]CCl>>[Cl-:57].[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20](=[O:21])[C:19]([CH2:28][O:29][C:30](=[O:43])[C@@H:31]([NH3+:35])[CH:32]([CH3:34])[CH3:33])([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:18]([CH3:44])[C:17]2=[O:45])=[CH:12][C:11]=1[C:46]([F:48])([F:47])[F:49])#[N:9]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67134659HCID 67134659, compound

Product 1

HCID 86667793HCID 86667793, compound

Procedure

3 mL of trifluoroacetic acid are added to a solution of 0.65 g of (2S)-2-[(1,1-dimethylethoxy)carbonylamino]-3-methylbutanoic acid (S)-[1-(4-cyano-3-trifluoromethylphenyl)-2,5-dioxo-3-methyl-4-phenylimidazolidin-4-yl]methyl ester in 30 mL of dichloromethane. The mixture is stirred at room temperature for 5 hours, 20 mL of toluene are added then the solvent is evaporated to dryness. The crude product is diluted with a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and evaporated. The crude product is dissolved in 120 mL of dichloromethane/ethyl ether mixture (10/90) and 0.75 mL of a 2M hydrogen chloride solution in ethyl ether is added. After filtration, the desired compound is obtained

Workup

  1. customthe solvent is evaporated to dryness
  2. additionThe crude product is diluted with a saturated aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe crude product is dissolved in 120 mL of dichloromethane/ethyl ether mixture (10/90)
  8. addition0.75 mL of a 2M hydrogen chloride solution in ethyl ether is added
  9. filtrationAfter filtration

Sources & evidence

ORD record
ord-ecd7e3f4c7eb4ae282236d8132268fa5
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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