Acetamide → HCID 67376749, compound

HRID 1408304Notes

Reaction equation

HRID 1408304 reaction equation
[CH2:1]([O:7][C:8]1[CH:29]=[CH:28][C:11]([C:12]([O:14][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=2)=O)=O)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([NH2:33])(=O)C.B(F)(F)F>>[CH2:1]([O:7][C:8]1[CH:29]=[CH:28][C:11]([C:12]2[O:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=3)[N:33]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 3

HCID 178AcetamideHCID 6356Boron trifluoride2×HCID 67376700HCID 67376700, compound

Product 1

HCID 67376749HCID 67376749, compoundYield 18%

Conditions

Temperature
140 °C

Procedure

140 mg (0.377 mmol) 2-[4-(methoxycarbonyl)phenyl]-2-oxoethyl 4-hexyloxybenzoate and 111 mg (5 eq) acetamide were dissolved in 5 mL xylenes. 10 uL (0.2 eq) boron trifluoride was added and the reaction was stirred at 140° C. for 18 h. Another 50 uL (1.0 eq) boron trifluoride was added and stirring continued for 24 h. The reaction was quenched with saturated sodium bicarbonate solution and extracted with DCM. The combined organic phases were dried and evaporated. Purification of the residue by flash chromatography (100% hexanes to 10% EA/hexanes) yielded 26 mg (0.068 mmol, 18%) of the product. MS: m/z=380.21 [M+1]+.

Workup

  1. stirringstirring
  2. waitcontinued for 24 h
  3. customThe reaction was quenched with saturated sodium bicarbonate solution
  4. extractionextracted with DCM
  5. customThe combined organic phases were dried
  6. customevaporated
  7. customPurification of the residue by flash chromatography (100% hexanes to 10% EA/hexanes)

Sources & evidence

ORD record
ord-19c3e625334c4475a25329b082ed728b
Source dataset
uspto-grants-2014_12
Patent number
US08921309B2

Reaction notes

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