Triethylamine → HCID 3013676, compound

HRID 412928Notes

Reaction equation

HRID 412928 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]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.[CH3:39][S:40](Cl)(=[O:42])=[O:41].C(=O)([O-])O.[Na+]>C1COCC1>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:18]([CH:20]2[CH2:25][CH2:24][N:23]([S:40]([CH3:39])(=[O:42])=[O:41])[CH2:22][CH2:21]2)=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 3013672HCID 3013672, compound2×

Product 1

HCID 3013676HCID 3013676, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound obtained in Example 2 (252 mg, 0.60 mmol) and triethylamine (0.201 ml) were dissolved in THF (5 ml), and under ice cooling, to the solution was added methanesulfonyl chloride (0.093 ml). The mixture was stirred at the same temperature for 1 hour. The compound obtained in Example 2 (252 mg, 0.60 mmol) and triethylamine (0.201 ml) were dissolved in THF (5 ml). To the solution was added methanesulfonyl chloride (0.093 ml) under ice cooling with stirring, and the mixture was stirred at the same temperature for 1 hour. To the 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 magnesium 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), and the desired fraction was concentrated under reduced pressure. To the concentrate was added diisopropyl ether (10 ml), and the resulting precipitates were collected by filtration. The precipitates were washed with diisopropyl ether, and dried under reduced pressure to give the titled compound,(110 mg, 0.22 mmol, Yield 37%) as white crystals.

Workup

  1. stirringwith stirring
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate (15 ml×3)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationthe desired fraction was concentrated under reduced pressure
  7. additionTo the concentrate was added diisopropyl ether (10 ml)
  8. customthe resulting precipitates
  9. filtrationwere collected by filtration
  10. washThe precipitates were washed with diisopropyl ether
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-18176bb3b8ba42bd8517e765130c69b7
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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