Acetyl chloride → HCID 18538454, compound

HRID 1394354Notes

Reaction equation

HRID 1394354 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.[C:40](Cl)(=[O:42])[CH3:41].C(=O)([O-])O.[Na+]>C1COCC1>[C:40]([N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:18](=[O:19])[N:17]([CH2:16][CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][CH:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][CH2:12]2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:22][CH2:23]1)(=[O:42])[CH3:41]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 18538613HCID 18538613, compound

Product 1

HCID 18538454HCID 18538454, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 13 (435 mg, 1.00 mmol), triethylamine (0.335 ml) were dissolved in THF (10 ml), and under ice cooling, to the solution was added acetyl chloride (0.142 ml). 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 collected by filtration. The filtrate was concentrated under reduced pressure. To the concentrate was added diethyl ether, and the resulting precipitates were collected by filtration. The precipitates were washed with diethyl ether, and dried under reduced pressure to give the titled compound (331 mg, 0.69 mmol, Yield 69%) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (15 ml×3)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. concentrationthe desired fraction was concentrated under reduced pressure
  5. additionTo the concentrate was added ethyl acetate
  6. customresulting
  7. customprecipitates
  8. filtrationwere collected by filtration
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. additionTo the concentrate was added diethyl ether
  11. customthe resulting precipitates
  12. filtrationwere collected by filtration
  13. washThe precipitates were washed with diethyl ether
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-75efc3f4345a422eaf228f6787afabcf
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

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