Triethylamine → HCID 18539173, compound

HRID 412942Notes

Reaction equation

HRID 412942 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]([CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]2)[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[F:38][C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1.C(=O)([O-])O.[Na+]>ClCCl.C1COCC1>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:21][CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH:27]([NH:30][S:45]([C:42]3[CH:43]=[CH:44][C:39]([F:38])=[CH:40][CH:41]=3)(=[O:47])=[O:46])[CH2:28][CH2:29]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 18538943HCID 18538943, compound

Product 1

HCID 18539173HCID 18539173, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the mixture of the compound obtained in Example 194 (528 mg, 1.00 mmol), triethylamine (0.502 mL, 3.60 mmol), THF (10 mL) and dichloromethane (10 mL) was added 4-fluorobenzenesulfonyl chloride (234 mg, 1.20 mmol), and the mixture was stirred at room temperature for 16 hours. To the mixture was added a saturated aqueous solution of sodium hydrogen carbonate (15 ml), and the organic solvent was distilled off under reduced pressure. The aqueous layer was extracted with ethyl acetate (15 mL×3). The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate (5 mL×3), saturated sodium chloride solution (5 mL), successively, dried over magnesium sulfate and concentrated under reduced pressure. The concentrate was subjected to column chromatography (silica gel log, ethyl acetate/methanol=1/0 to 9/1), 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 give the titled compound (516 mg, 0.84 mmol, Yield 84%) as colorless foam like substance.

Workup

  1. distillationthe organic solvent was distilled off under reduced pressure
  2. extractionThe aqueous layer was extracted with ethyl acetate (15 mL×3)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate (5 mL×3), saturated sodium chloride solution (5 mL)
  4. dry with materialsuccessively, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationthe desired fraction was concentrated under reduced pressure
  7. additionTo the concentrate was added ethyl acetate
  8. customresulting
  9. customprecipitates
  10. filtrationwere filtered off
  11. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-befb136a5aad4d0d96195886ec44a68f
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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