Acetyl chloride → HCID 25197049, compound

HRID 1876313Notes

Reaction equation

HRID 1876313 reaction equation
[CH:1]1([NH:6][C:7]2[CH:8]=[C:9]([F:25])[CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([C:16]2[S:17][CH2:18][C@@H:19]([CH2:21][C:22]([OH:24])=[O:23])[N:20]=2)=[CH:12]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:26](Cl)(=O)[CH3:27]>C(O)C.C(OCC)(=O)C>[CH2:26]([O:23][C:22](=[O:24])[CH2:21][C@@H:19]1[CH2:18][S:17][C:16]([C:13]2[NH:14][C:15]3[C:11]([CH:12]=2)=[CH:10][C:9]([F:25])=[CH:8][C:7]=3[NH:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[N:20]1)[CH3:27]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 59543018HCID 59543018, compound

Product 1

HCID 25197049HCID 25197049, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (80 mg, 0.22 mmol) prepared in Example 37 was dissolved in ethanol (2 ml). Acetyl chloride (0.1 ml) was added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, the reaction solution was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and purified by column chromatography to give the title compound (50 mg, Yield 58%).

Workup

  1. customAfter completion of the reaction
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-01ecfa4a12cb4720a6f1b5ba7b29bf8d
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

Loading…