Triethylamine → HCID 86631209, compound

HRID 252999Notes

Reaction equation

HRID 252999 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:21][CH2:20][CH2:19][C@H:18]2[CH2:22]O)=[O:16])=[CH:11][CH:10]=1.CS(Cl)(=O)=O.C(=O)([O-])O.[Na+].[C:34]([O-:37])(=[S:36])[CH3:35].[K+]>C(Cl)(Cl)Cl.CN(C)C=O>[C:34](=[O:37])([S:36][CH2:22][C@@H:18]1[CH2:19][CH2:20][CH2:21][N:17]1[C:15](=[O:16])[C:12]1[CH:11]=[CH:10][C:9]([Br:8])=[CH:14][CH:13]=1)[CH3:35]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate2×HCID 23670855Potassium ethanethioateHCID 28345615HCID 28345615, compound

Product 1

HCID 86631209HCID 86631209, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.2 ml, 1.41 mmol) was added to a solution of 200 mg (0.704 mmol) of (S)-(4-bromophenyl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone synthesized in step (i) of Reference Example 8 in chloroform (2 ml), and the mixture was stirred at room temperature for 10 min. Thereafter, 0.11 ml (1.41 mmol) of methanesulfonyl chloride was added thereto, and the mixture was stirred at room temperature for 10 min. The reaction was stopped by adding a saturated aqueous sodium hydrogencarbonate solution, and the reaction solution was extracted with chloroform. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate, and was then filtered. The filtrate was concentrated under the reduced pressure and was then dried. Potassium thioacetate (160.8 mg, 1.41 mmol) was added to a solution of the crude product in N,N-dimethylformamide (4 ml), and the mixture was stirred at 100° C. for 2 hr. The reaction was stopped by adding a saturated aqueous sodium hydrogencarbonate solution, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate, and was then filtered. The filtrate was concentrated under the reduced pressure, and the residue was then purified by preparative thin layer chromatography (hexane:ethyl acetate=1:2) to give 100 mg (yield 42%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. extractionthe reaction solution was extracted with chloroform
  3. washThe organic layer was washed with water and saturated brine in that order
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationwas then filtered
  6. concentrationThe filtrate was concentrated under the reduced pressure
  7. customwas then dried
  8. stirringthe mixture was stirred at 100° C. for 2 hr
  9. extractionthe reaction solution was extracted with ethyl acetate
  10. washThe organic layer was washed with water and saturated brine in that order
  11. dry with materialwas dried over anhydrous sodium sulfate
  12. filtrationwas then filtered
  13. concentrationThe filtrate was concentrated under the reduced pressure
  14. customthe residue was then purified by preparative thin layer chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-056bae51634f4fe2a921c79d22f20e04
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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