Triethylamine → HCID 22272819, compound

HRID 1064842Notes

Reaction equation

HRID 1064842 reaction equation
[CH:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([CH:12]([CH3:14])[CH3:13])[C:5]=1[NH:15][C:16](=[O:28])[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26]O)[CH2:20][CH2:19]1)([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[Cl:41][C:42]1[CH:43]=[C:44]([CH:53]([CH3:55])[CH3:54])[C:45]2[O:49][C:48]([SH:50])=[N:47][C:46]=2[C:51]=1[CH3:52].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1.CN(C)C1C=CN=CC=1.O>[Cl:41][C:42]1[CH:43]=[C:44]([CH:53]([CH3:55])[CH3:54])[C:45]2[O:49][C:48]([S:50][CH2:26][CH2:25][CH2:24][N:21]3[CH2:20][CH2:19][N:18]([CH2:17][C:16]([NH:15][C:5]4[C:6]([CH:12]([CH3:13])[CH3:14])=[CH:7][CH:8]=[C:9]([O:10][CH3:11])[C:4]=4[CH:1]([CH3:2])[CH3:3])=[O:28])[CH2:23][CH2:22]3)=[N:47][C:46]=2[C:51]=1[CH3:52]

Participants

10

Reactant 6

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 31297Methanesulfonyl chlorideHCID 69730844HCID 69730844, compoundHCID 178427920HCID 178427920, compound

Product 1

HCID 22272819HCID 22272819, compoundYield 39%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of the alcohol (150 mg, 0.38 mmol) in THF (3 ml) were added triethylamine (50 mg, 0.50 mmol) and 4-dimethylaminopyridine (5 mg, 0.04 mmol), then methanesulfonyl chloride (53 mg, 0.46 mmol) was dropped thereinto with ice cooling and stirring, the mixture was stirred for 30 minutes. After the reaction, the reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was evaporated. The resulting residue was dissolved in DMF (5 ml), then 5-chloro-7-isopropyl-2-mercapto-4-methylbenzoxazole (93 mg, 0.38 mmol), potassium carbonate (64 mg, 0.46 mmol) and 18-crown-6 (10 mg, 0.04 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, dried over anhydrous sodium sulfate and the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=50:1) and the resulting crystals were recrystallized from ethyl acetate-hexane to provide 91 mg (yield 39%) of the desired compound as colorless powdery crystals.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customAfter the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. dissolutionThe resulting residue was dissolved in DMF (5 ml)
  8. stirringthe mixture was stirred at 80° C. for 1 hour
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with water
  11. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  12. customthe solvent was evaporated
  13. customThe resulting residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=50:1)
  14. customthe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-380766cb11374a4582fbb49a60c25c11
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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