Chloroacetyl chloride → HCID 67597500, compound

HRID 1740865Notes

Reaction equation

HRID 1740865 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][NH:4][CH2:5][C@@H:6]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH2:8][CH2:9][CH3:10].C(=O)(O)[O-].[Na+].Cl[CH2:27][C:28](Cl)=[O:29].C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[C:15]([O:14][C:12]([N:11]1[CH2:27][C:28](=[O:29])[N:4]([CH2:3][C:2]([F:19])([F:20])[F:1])[CH2:5][C@@H:6]1[CH2:7][CH2:8][CH2:9][CH3:10])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 18393366HCID 18393366, compound

Product 1

HCID 67597500HCID 67597500, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the product from Step C (0.590 g, 1.98 mmol) in ethyl acetate (30 mL) was vigorously stirred at 0° C. with saturated sodium bicarbonate (30 mL). Chloroacetyl chloride (0.315 mL, 3.96 mmol) was added, and the reaction stirred at 0° C. for 1 h. The layers were separated, and the ethyl acetate phase was washed with saturated brine, and dried over magnesium sulfate. The crude product was dissolved in DMF (15 mL) and cooled to 0° C. under nitrogen. Cesium carbonate (1.67 g, 5.12 mmol) was added and the reaction stirred 1 h at 0° C., then at room temperature overnight. The reaction was quenched with amminium chloride, and partitioned between ethyl acetate and water. The organic phase was washed with water, saturated brine, and dried over magnesium sulfate. The title compound was obtained as a colorless oil.

Workup

  1. customThe layers were separated
  2. washthe ethyl acetate phase was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. dissolutionThe crude product was dissolved in DMF (15 mL)
  5. temperaturecooled to 0° C. under nitrogen
  6. stirringthe reaction stirred 1 h at 0° C.
  7. customat room temperature
  8. customovernight
  9. customThe reaction was quenched with amminium chloride
  10. custompartitioned between ethyl acetate and water
  11. washThe organic phase was washed with water, saturated brine
  12. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-d952ed4e85c24a91909f9f30f91699f2
Source dataset
uspto-grants-1999_10
Patent number
US05972942

Reaction notes

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