Sodium hydride → (S)-2-(2-t-butoxycarbonylaminopropylthio)-3-phenylquinoline

HRID 1903234Notes

Reaction equation

HRID 1903234 reaction equation
[C:1]1([C:7]2[C:8](=[S:17])[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].[C:22]([O:26][C:27]([NH:29][C@@H:30]([CH3:43])[CH2:31]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O>[C:22]([O:26][C:27]([NH:29][C@@H:30]([CH3:43])[CH2:31][S:17][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 132002063-Phenylquinolin-2-thioneHCID 13200311(S)-2-((tert-butoxycarbonyl)amino)propyl 4-methylbenzenesulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 13200313(S)-2-(2-t-butoxycarbonylaminopropylthio)-3-phenylquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Phenylquinolin-2-thione (2.5 g.) was added to a suspension of sodium hydride (0.55 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (16 ml.) at 0°-5°. When all the hydrogen had evolved, (S)-2-t-butoxycarbonylamino-1-p-toluenesulphonyloxypropane (3.5 g.) was added and the mixture was stirred at ambient temperature for 16 hr. The mixture was then poured into ice-water (160 ml.) and extracted with ethyl acetate (3×50 ml.). The ethyl acetate extract was washed with brine (50 ml.) and then dried (MgSO4). The solvent was evaporated and the residue was crystallised from petroleum ether to give (S)-2-(2-t-butoxycarbonylaminopropylthio)-3-phenylquinoline, m.p. 86°-7°.

Workup

  1. customat 0°-5°
  2. extractionextracted with ethyl acetate (3×50 ml.)
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine (50 ml.)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was crystallised from petroleum ether

Sources & evidence

ORD record
ord-a4e802de81e54b4794cce991d53bb269
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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