Acetyl chloride → HCID 69885714, compound

HRID 1862575Notes

Reaction equation

HRID 1862575 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][O:20][CH2:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36].S([O-])(O)(=O)=O.[Na+]>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][O:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25]([C:35](=[O:37])[CH3:36])[CH2:24][CH2:23]3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516919Sodium BisulfateHCID 18619999HCID 18619999, compound

Product 1

HCID 69885714HCID 69885714, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 20 ml of dichloromethane, was dissolved 298 mg of the compound obtained in Example 16. To the resulting solution, was added 3.0 ml of triethylamine. To the obtained mixture, 0.46 ml of acetyl chloride was added under cooling with ice and stirring. The mixture was stirred at 0° C. to room temperature for 18 hours. The obtained mixture was poured into a saturated aqueous solution of sodium hydrogensulfate and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine and subsequently dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to afford 260 mg (78%) of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was stirred at 0° C. to room temperature for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  5. dry with materialsubsequently dried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe obtained crude product
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9827e698158e4b75b93af5afaa40d021
Source dataset
uspto-grants-2003_03
Patent number
US06538137B1

Reaction notes

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