Chloroacetyl chloride → HCID 123621071, compound

HRID 1893607Notes

Reaction equation

HRID 1893607 reaction equation
[NH2:1][C:2](=[N:42][OH:43])[C:3]1[CH:4]=[CH:5][C:6]([CH3:41])=[C:7]([N:9]([CH2:26][C:27]([N:29]([N:31]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([F:40])[CH:37]=3)[CH2:32]2)[CH3:30])=[O:28])[CH2:10][C:11]([NH:13][CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH3:18])=[O:12])[CH:8]=1.[O-2].[Mg+2].[Cl:46][CH2:47][C:48](Cl)=O>O1CCOCC1.C(OCC)(=O)C>[Cl:46][CH2:47][C:48]1[O:43][N:42]=[C:2]([C:3]2[CH:4]=[CH:5][C:6]([CH3:41])=[C:7]([N:9]([CH2:26][C:27]([N:29]([N:31]3[CH2:39][C:38]4[C:33](=[CH:34][CH:35]=[C:36]([F:40])[CH:37]=4)[CH2:32]3)[CH3:30])=[O:28])[CH2:10][C:11]([NH:13][CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:17][CH3:18])=[O:12])[CH:8]=2)[N:1]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6850729Magnesium monoxideHCID 123265661HCID 123265661, compound

Product 1

HCID 123621071HCID 123621071, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The compound (4.82 g, 8.04 mmol) of Example 290, step B was dissolved in 1,4-dioxane (70 ml), magnesium oxide (355 mg, 8.81 mmol) and chloroacetyl chloride (0.67 ml, 8.42 mmol) were added at room temperature, and the mixture was stirred at 100° C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, and the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (3.40 g, yield 64%) as a pale-yellow amorphous solid

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe solution was concentrated under reduced pressure
  6. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0c5d7b2cd8af4698bc664037cf301c34
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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