Triethylamine → HCID 90449543, compound

HRID 1411305Notes

Reaction equation

HRID 1411305 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:14]3([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]3)[CH2:13][N:12]([C:26]([O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])=[O:27])[C:9]2=[CH:10][CH:11]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:47][C:48]([S-:50])=[O:49].[K+]>O1CCCC1.O>[C:48]([S:50][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:14]3([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:15]3)[CH2:13][N:12]([C:26]([O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])=[O:27])[C:9]2=[CH:10][CH:11]=1)(=[O:49])[CH3:47]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 4463282Potassium thioacetateHCID 90449964HCID 90449964, compound

Product 1

HCID 90449543HCID 90449543, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-(4-hydroxybutyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (120.7 mg, 0.246 mmol) was dissolved in tetrahydrofuran (2.5 mL). Thereafter, triethylamine (46 μL, 0.32 mmol) and methanesulfonyl chloride (21 μL, 0.27 mmol) were added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at room temperature for 1 hour. Thereafter, insoluble matters were filtered, and the filtrate was then concentrated in vacuo. The residue was dissolved in N,N-dimethylformamide (2.4 mL), and S-potassium thioacetate (62 mg, 0.54 mmol) was then added to the above solution. The thus obtained mixture was stirred at room temperature for 15 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was washed with water and brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=5:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(4-(acetylthio)butyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (89.2 mg, 66%) in the form of a brown oily product.

Workup

  1. temperatureunder cooling on ice
  2. filtrationThereafter, insoluble matters were filtered
  3. concentrationthe filtrate was then concentrated in vacuo
  4. dissolutionThe residue was dissolved in N,N-dimethylformamide (2.4 mL)
  5. stirringThe thus obtained mixture was stirred at room temperature for 15 hours
  6. extractionthe mixed solution was then extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialwas then dried over anhydrous sodium sulfate
  9. concentrationfollowed by concentration in vacuo
  10. customThe obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=5:1)

Sources & evidence

ORD record
ord-3437c81277fb40e5adb3f46a8570c401
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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