Hydrochloric Acid → HCID 69080162, compound

HRID 594398Notes

Reaction equation

HRID 594398 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]1[CH:14](C(OCC)=O)[C:13](=[O:20])[C:12](=[O:21])[N:11]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1.Cl.C(Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]1[N:11]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:27][CH:28]=2)[C:12](=[O:21])[C:13](=[O:20])[CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 69081459HCID 69081459, compound

Product 1

HCID 69080162HCID 69080162, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 2-(2-fluoro-6-methoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-3-carboxylate (2.937 g; 6.26 mmol) in dioxane (13 ml) was treated with 25% hydrochloric acid (13 ml). The resulting mixture was then refluxed, under nitrogen, for 11 h. After cooling to rt, DCM and aq. sat. NaHCO3 were added. The separated aqueous layer was further extracted with DCM. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 5-(2-fluoro-6-methoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione which was used for the next step without additional purification. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 397.99 g/mol.

Workup

  1. temperatureThe resulting mixture was then refluxed, under nitrogen, for 11 h
  2. extractionThe separated aqueous layer was further extracted with DCM
  3. washThe mixed organic layers were washed with brine
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-cc5cdbf36fad44c0b9b00777c6f762ad
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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