Triethylamine → HCID 18539085, compound

HRID 412932Notes

Reaction equation

HRID 412932 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:18]([NH:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42].C(=O)([O-])O.[Na+]>C1COCC1>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][N:17]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:18]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:23][CH2:22]2)=[O:19])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 18538613HCID 18538613, compound

Product 1

HCID 18539085HCID 18539085, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 13 (435 mg, 1.00 mmol) and triethylamine (0.335 ml) were dissolved in THF (10 ml). To the solution was added methanesulfonyl chloride (0.155 ml) under ice cooling with stirring, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate (15 ml) under ice cooling, and the mixture was extracted with ethyl acetate (15 ml×3). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to column chromatography (silica gel 10 g, ethyl acetate/methanol=1/0 to 9/1 to 4/1), and the desired fraction was concentrated under reduced pressure. To the concentrate was added ethyl acetate and resulting precipitates were filtered off. The filtrate was concentrated under reduced pressure. To the concentrate was added diethyl ether and resulting precipitates were collected by filtration The precipitates were washed with diethyl ether, and dried under reduced pressure to give the titled compound (310 mg, 0.60 mmol, Yield 60%) as white solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate (15 ml×3)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. concentrationthe desired fraction was concentrated under reduced pressure
  6. additionTo the concentrate was added ethyl acetate
  7. customresulting
  8. customprecipitates
  9. filtrationwere filtered off
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. additionTo the concentrate was added diethyl ether
  12. customresulting
  13. customprecipitates
  14. filtrationwere collected by filtration The precipitates
  15. washwere washed with diethyl ether
  16. customdried under reduced pressure

Sources & evidence

ORD record
ord-b62b255de5e04443a869c3f2ea94210f
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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