Triethylamine → HCID 9848030, compound

HRID 1064794Notes

Reaction equation

HRID 1064794 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:25])[CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23]O)[CH2:18][CH2:17]1)([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[SH:38][C:39]1[O:40][C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1.CN(C)C1C=CN=CC=1.O>[O:40]1[C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=[C:39]1[S:38][CH2:23][CH2:22][N:19]1[CH2:18][CH2:17][N:16]([CH2:15][C:14]([NH:13][C:5]2[C:6]([CH:10]([CH3:12])[CH3:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH:1]([CH3:2])[CH3:3])=[O:25])[CH2:21][CH2:20]1

Participants

10

Reactant 6

HCID 8471Triethylamine2×HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 31297Methanesulfonyl chloride2×HCID 22272598HCID 22272598, compoundHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 9848030HCID 9848030, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of this alcohol (300 mg, 0.86 mmol) in THF (5 ml) were added triethylamine (172 mg, 1.7 mmol) and 4-dimethylaminopyridine (10 mg, 0.09 mmol), then methanesulfonyl chloride (115 mg, 1.0 mmol) was dropped there into with ice-cooling and stirring, and the mixture was stirred for 40 minutes. After that, triethylamine (172 mg, 1.7 mmol) was further added thereto, then methanesulfonyl chloride (115 mg, 1.0 mmol) was dropped thereinto with ice-cooling and stirring, and the mixture was stirred for 20 minutes. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, an aqueous solution of sodium bicarbonate and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate, and the solvent was evaporated therefrom. The resulting residue was dissolved in DMF (7 ml), then 2-mercaptobenzooxazole (130 mg, 0.86 mmol), potassium carbonate (180 mg, 1.3 mmol) and 18-crown-6 (21 mg, 0.08 mmol) were added thereto, and the mixture was stirred at 80° C. for 1 hour. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (40 g of silica gel; developing solvent, hexane:acetone=5:1˜10:3) and the resulting crystals were recrystallized from acetone-hexane to provide 326 mg (yield 79%) of the desired compound as colorless needles.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 40 minutes
  3. temperaturewith ice-cooling
  4. stirringstirring
  5. stirringthe mixture was stirred for 20 minutes
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialan aqueous solution of sodium bicarbonate and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate
  9. customthe solvent was evaporated
  10. dissolutionThe resulting residue was dissolved in DMF (7 ml)
  11. stirringthe mixture was stirred at 80° C. for 1 hour
  12. extractionextracted with ethyl acetate
  13. washThe organic layer was washed with water
  14. dry with materiala saturated sodium chloride solution successively and dried over anhydrous sodium sulfate
  15. customthe solvent was evaporated
  16. customThe residue was purified by a silica gel column chromatography (40 g of silica gel; developing solvent, hexane:acetone=5:1˜10:3)
  17. customthe resulting crystals were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-63c298deacf945b183ecdf2d093a0132
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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