HCID 86711945, compound → HCID 86711946, compound

HRID 1475254Notes

Reaction equation

HRID 1475254 reaction equation
O=[C:2]([NH:8][CH2:9][C:10](=[O:22])[C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]>O=P(Cl)(Cl)Cl>[F:21][C:18]([F:19])([F:20])[O:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[O:22][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:8][CH:9]=2)=[CH:16][CH:15]=1

Participants

3

Reactant 1

HCID 86711945HCID 86711945, compound

Product 1

HCID 86711946HCID 86711946, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of ethyl 2-oxo-2-(2-oxo-2-(4-(trifluoromethoxy)phenyl)ethylamino)acetate (7.8 g, 24.4 mmol) in POCl3 (50 mL) was heated at 110° C. for 3 h, and then cooled to RT. The mixture was concentrated under reduced pressure, diluted with ice—H2O (100 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with H2O (2×50 mL), brine (30 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1 to 2:1) to give the title compound as a light yellow solid (6.4 g, 87%). MS (ES+) C13H10F3NO4 requires: 301. found: 302 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with ice—H2O (100 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organic layers were washed with H2O (2×50 mL), brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1 to 2:1)

Sources & evidence

ORD record
ord-827647147d19496faf0ddfa10448c8f7
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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